Bromide ion → 2-Bromo-4,5,6,7-tetrahydro(1,3)thiazolo(5,4-c)pyridine, N-BOC protected

HRID 418343Notes

Reaction equation

C(ON=O)C(C)C.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][C:18]2[N:21]=[C:22](N)[S:23][C:17]=2[CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].[Br-:25]>CN(C=O)C>[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][C:18]2[N:21]=[C:22]([Br:25])[S:23][C:17]=2[CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 60 °C

Procedure

Suspended CuBr2 (905 mg, 4.05 mmol) in 5 mL of DMF and added i-butylnitrite (0.57 mL), 4.86 mmol). To this was added 2-amino-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid tert-butyl ester (860 mg, 3.36 mmol) and the mixture was stirred for 2 h at 60° C. LC-MS analysis indicated the desired bromide. Concentrated the mixture to a brown-red residue. Dissolved the residue in CH2Cl2 and purified via SiO2 chromatography (EtOAc/hexanes 0-20%) to give 650 mg of 2-bromo-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid tert-butyl ester.

Workup

concentrationConcentrated the mixture to a brown-red residue
dissolutionDissolved the residue in CH2Cl2
custompurified via SiO2 chromatography (EtOAc/hexanes 0-20%)

Sources & evidence

ORD record: ord-a5eda44551a14edaba745bfc46bf6d2d
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093266B2

Reaction notes

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