Methanol → (r)-n-(2-Aminoindan-5-yl)-6-methyl-4'-trifluoromethylbiphenyl-2-carboxamide

HRID 1814784Notes

Reaction equation

HRID 1814784 reaction equation
COC([NH:5][C@H:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:15][C:16]([C:18]3[C:19]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)=[O:17])[CH:12]=2)[CH2:7]1)=O.I[Si](C)(C)C.CO>C(#N)C>[NH2:5][C@H:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:15][C:16]([C:18]3[C:19]([C:25]4[CH:26]=[CH:27][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:29][CH:30]=4)=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)=[O:17])[CH:12]=2)[CH2:7]1

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 9869236(r)-6-Methyl-4'-trifluoromethylbiphenyl-2-carboxylic acid (2-methoxycarbonylaminoindan-5-yl)-amide

Product 1

HCID 11112358(r)-n-(2-Aminoindan-5-yl)-6-methyl-4'-trifluoromethylbiphenyl-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

(R)-6-methyl-4′-trifluoromethyl-1,1′-biphenyl-2-carboxylic acid (2-methoxycarbonylaminoindan-5-yl)-amide (6.5 g, 13.9 mmol) is dissolved in acetonitrile (325 mL) and cooled to 0° C. under nitrogen. Iodotrimethylsilane (11.1 g, 55.6 mmol) is added dropwise, the mixture is allowed to warm to room temperature and is stirred overnight. Methanol (100 mL) is added and the mixture is stirred for 1 hour and then concentrated in vacuo. The residue is dissolved in ethyl acetate (750 mL) and washed with saturated sodium bicarbonate (2×125 mL), water (125 mL), 5% Na2S2O3 solution (125 mL), water (125 mL), and brine (50 mL). The organic phase is dried over sodium sulfate and concentrated to afford (R)-N-(2-aminoindan-5-yl)-6-methyl-4′-trifluoromethyl-1,1′-biphenyl-2-carboxamide.

Workup

  1. temperatureto warm to room temperature
  2. stirringthe mixture is stirred for 1 hour
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue is dissolved in ethyl acetate (750 mL)
  5. washwashed with saturated sodium bicarbonate (2×125 mL), water (125 mL), 5% Na2S2O3 solution (125 mL), water (125 mL), and brine (50 mL)
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-df54a52d7ad840458e926211588bd59e
Source dataset
uspto-grants-2005_04
Patent number
US06878707B2

Reaction notes

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