Trifluoroacetic acid → 2-(4-amino-phenyl)-1-cyclobutyl-6-methanesulfonylmethoxy-1H-indole-3-carbonitrile

HRID 502281Notes

Reaction equation

HRID 502281 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]([CH:31]3[CH2:34][CH2:33][CH2:32]3)[C:16]3[C:21]([C:22]=2[C:23]#[N:24])=[CH:20][CH:19]=[C:18]([O:25][CH2:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:17]=3)=[CH:10][CH:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:15]([CH:31]3[CH2:34][CH2:33][CH2:32]3)[C:16]3[C:21]([C:22]=2[C:23]#[N:24])=[CH:20][CH:19]=[C:18]([O:25][CH2:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:17]=3)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59606451[4-(3-Cyano-1-cyclobutyl-6-methanesulfonylmethoxy-1H-indol-2-yl)-phenyl]-carbamic acid tert-butyl ester

Product 1

HCID 684271882-(4-amino-phenyl)-1-cyclobutyl-6-methanesulfonylmethoxy-1H-indole-3-carbonitrileYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To [4-(3-Cyano-1-cyclobutyl-6-methanesulfonylmethoxy-1H-indol-2-yl)-phenyl]-carbamic acid tert-butyl ester (1.21 g, 2.47 mmol) in CH2Cl2 (6 mL) was added TFA (2 mL) and stirred at room temperature for 1 h. The reaction mixture was diluted in CH2Cl2, washed with aq. NaHCO3, dried and concentrated. Trituration with acetone (5 mL) provided 2-(4-amino-phenyl)-1-cyclobutyl-6-methanesulfonylmethoxy-1H-indole-3-carbonitrile (891 mg, 91%) as a light pink solid.

Workup

  1. washwashed with aq. NaHCO3
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5baf186090934e32b3305d26c99d75ca
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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