2-Bromothiazole → HCID 59787364, compound

HRID 911563Notes

Reaction equation

Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[C:7]([O:11][C:12]([N:14]1[CH2:20][CH2:19][C:18]2[C:21]([C:26]#[CH:27])=[C:22]([Cl:25])[CH:23]=[CH:24][C:17]=2[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>>[C:7]([O:11][C:12]([N:14]1[CH2:20][CH2:19][C:18]2[C:21]([C:26]#[C:27][C:2]3[S:3][CH:4]=[CH:5][N:6]=3)=[C:22]([Cl:25])[CH:23]=[CH:24][C:17]=2[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

Reactant 2

HCID 764302-Bromothiazole

HCID 59787377HCID 59787377, compound

Product 1

HCID 59787364HCID 59787364, compoundYield 89%

Procedure

Use a method similar to the General Procedure 8 to couple 2-bromo-thiazole (0.09 mL, 0.96 mmol) with 3-tert-butoxycarbonyl-7-chloro-6-ethynyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (148 mg, 0.48 mmol). Purify by chromatography on silica gel eluting with isohexane/EtOAc (1:0 to 4:1 gradient over 30 min) to give the desired intermediate (165 mg, 89%). MS (ES+) m/z: 389 (M+H)+.

Workup

customPurify by chromatography on silica gel eluting with isohexane/EtOAc (1:0 to 4:1 gradient over 30 min)

Sources & evidence

ORD record: ord-357dd7477bb945ec839d1f5b1e1e62c0
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022062B2

Reaction notes

Loading…