KBS24-2 - Click coupling of bis-propargyl-1,6-diaminohexane and azidomethylferrocene

[KlementineJBS]

Link to HIRAC, original method and [master page].

KBS24 Linear amine click coupling with azidomethylferrocene.docx

Previous attempt is #44

Reaction scheme

Outcome

[KlementineJBS]

1. Dissolved copper sulphate pentahydride (14.8 mg, 0.059 mmol, 0.3 equiv.) and sodium ascorbate (25.6 mg, 0.129 mmol, 0.6 equiv.) in sparged water (5 mL)
2. Evacuated and backfilled with nitrogen (x5)
3. Added KBS17 (89.7 mg, 0.229 mmol) dissolved in sparged THF (3 mL)
4. Added KBS16 (132.1 mg, 0.548 mmol, 2.4 equiv.) dissolved in sparged THF (3 mL)
5. Left stirring under nitrogen from 10 am

[KlementineJBS]

KBS24-2 RM 07-03-23.pdf KBS24-2 RM 08-03-23 extended.pdf KBS24-2 RM 08-03-23.pdf

KBS24-2 RM.zip

[KlementineJBS]

13.03.23

Final TLC (5% MeOH in DCM). Reaction mixture had separated into two layers of green and orange.

Removed THF by rotovapping and worked up with DCM (3 x 15 mL). Washed with brine (30 mL), dried over mag sulphate and rotovapped down.

Empty vial: 15.9699 Full vial: 16.2223 Mass: 252.4 mg (0.289 mmol, >100%)

NMR

KBS24-2 cr_1.zip KBS24-2 cr.pdf

Appears pretty similar to previous NMR.

[KlementineJBS]

LRMS

KBS24-2 cr.pdf KBS24-2 crude.d.zip

[KlementineJBS]

Column

Fractions	Empty vial	Mass (mg)	Mass spec peaks	Assignation
3	15.5716	36.1	n/a	azidomethylferrocene
4	15.5545	50.7	618.27, 646.26, 897.33	product
5-7	15.6762	62.3	618.27, 646.26, 897.33	product
8-9	15.9234	20.8	n/a	unknown

LRMS

KBS24-2 F4-7.zip

KBS24-2 F4.pdf KBS24-2 F5-7.pdf

H NMR

KBS24-2 F3_1.zip KBS24-2 F4_1.zip KBS24-2 F5-7_1.zip KBS24-2 F8-9_1.zip

KBS24-2 column.pdf