Potassium Carbonate → 3-Amino-7-fluoro-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester

HRID 1366790Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][C:3]=1[F:10].C(=O)([O-])[O-].[K+].[K+].[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:18][SH:19]>CN(C=O)C>[CH2:22]([O:21][C:17]([C:18]1[S:19][C:2]2[C:3]([F:10])=[CH:4][N:5]=[CH:6][C:7]=2[C:8]=1[NH2:9])=[O:20])[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 4-chloro-5-fluoro-nicotinonitrile (1.0 g, 6.4 mmol) and potassium carbonate (4.4 g, 32 mmol) in DMF (15 mL) at 0° C. was added ethyl thioglycolate (0.73 mL, 6.7 mmol) dropwise. The reaction mixture was stirred at 0° C. for 10 min, at room temperature for 20 min and then at 40° C. for 30 min. The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was separated and washed with water followed by brine, dried over sodium sulphate and concentrated in vacuo to give the title compound as a yellow solid (1.5 g, quant.). LCMS (method B): RT=3.41 min, M+H+=241.

Workup

waitat 40° C. for 30 min
temperatureThe reaction mixture was cooled to room temperature
custompartitioned between water and ethyl acetate
customThe organic layer was separated
washwashed with water
dry with materialdried over sodium sulphate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7612dfa439524d6484e2428d1ef5679c
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893085B2

Reaction notes

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