(3,4-Difluoro-benzyl)-(3-methyl-benzo[b]thiophen-2-yl)-carbamic acid tert-butyl ester → (3,4-Difluoro-benzyl)-(3-methyl-benzo[b]thiophen-2-yl)-amine

HRID 1691546Notes

Reaction equation

HRID 1691546 reaction equation
C(OC(=O)[N:7]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=1)[C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]=1[CH3:17])(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[F:26][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[F:25])[CH2:18][NH:7][C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]=1[CH3:17]

Participants

4

Reactant 1

HCID 57920462(3,4-Difluoro-benzyl)-(3-methyl-benzo[b]thiophen-2-yl)-carbamic acid tert-butyl ester

Product 1

HCID 57920455(3,4-Difluoro-benzyl)-(3-methyl-benzo[b]thiophen-2-yl)-amine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of compound 125-C (2.7 g, 6.9 mmol) in dichloromethane (40 mL) and trifluoroacetic acid (40 mL) was stirred at rt for 4 h. The solvent was evaporated in vacuo, and the residue partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate, and the solvent evaporated in vacuo to afford compound 125-D as a colorless solid (1.86 g, 93%). 1H-NMR (CDCl3): δ 2.16 (s, 3H), 4.37 (s, 2H), 7.09-7.32 (m, 5H), 7.40 (d, 1H), 7.60 (d, 1H); MS: m/z 290.1 (MH+).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent evaporated in vacuo
  5. customto afford compound 125-D as a colorless solid (1.86 g, 93%)

Sources & evidence

ORD record
ord-97ea309fd5124e5b9f45915ea87a92eb
Source dataset
uspto-grants-2012_04
Patent number
US08153682B2

Reaction notes

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