Methyl Thioglycolate → Methyl 3-aminobenzo[b]thiophene-2-carboxylate

HRID 2102839Notes

Reaction equation

HRID 2102839 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:10]([O:14][CH3:15])(=[O:13])[CH2:11][SH:12].CC(C)([O-])C.[K+]>CN(C=O)C>[CH3:15][O:14][C:10]([C:11]1[S:12][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]=1[NH2:5])=[O:13]

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 678552-FluorobenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 874720Methyl 3-aminobenzo[b]thiophene-2-carboxylateYield 88.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-fluorobenzonitrile (9.0 g, 74.3 mmol) and methyl thioglycolate (13.3 mL, 148.6 mmol) in DMF (50 mL) at 0° C. was added potassium tert-butoxide portionwise (16.7 g. 149 mmol) over 15 min with vigorous stirring. The orange solution was warmed to rt and stirred for 1 h before being poured into 700 mL of vigorously stirring ice water. The precipitate was filtered and air-dried to give a pale yellow solid (13.6 g, 88%) that was used without purification. 1H NMR (CD3OD): 8.16-8.12 (m, 1H), 7.85-7.82 (m, 1H), 7.54-7.49 (m, 1H), 7.43-7.38 (m, 1H), 7.19 (s, 2H), 3.79 (s, 3H).

Workup

  1. filtrationThe precipitate was filtered
  2. customair-dried

Sources & evidence

ORD record
ord-f3e9db0ac82d47e1ae6907bdcf91f4de
Source dataset
uspto-grants-2009_08
Patent number
US07576092B2

Reaction notes

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