4,6-Dibromo-2,3-bis(methylsulfanyl)-1H-indole → 5-Amino-2-(4-trifluoromethyl-piperidin-1-yl)-N-cyclopropylmethylbenzamide

HRID 1846119Notes

Reaction equation

HRID 1846119 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:17]2[CH2:22][CH2:21][CH:20]([C:23]([F:26])([F:25])[F:24])[CH2:19][CH2:18]2)=[C:8]([CH:16]=1)[C:9]([NH:11][CH2:12][CH:13]1[CH2:15][CH2:14]1)=[O:10])([O-])=O.CSC1C2C(=CC(Br)=CC=2Br)NC=1SC>C1COCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:17]2[CH2:18][CH2:19][CH:20]([C:23]([F:26])([F:24])[F:25])[CH2:21][CH2:22]2)=[C:8]([CH:16]=1)[C:9]([NH:11][CH2:12][CH:13]1[CH2:14][CH2:15]1)=[O:10]

Participants

5

Reactant 2

HCID 141858534,6-Dibromo-2,3-bis(methylsulfanyl)-1H-indoleHCID 584834705-nitro-2-(4-trifluoromethyl-piperidin-yl)-N-cyclopropylmethylbenzamide

Product 1

HCID 584833895-Amino-2-(4-trifluoromethyl-piperidin-1-yl)-N-cyclopropylmethylbenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to example 42c with 5-nitro-2-(4-trifluoromethyl-piperidin-yl)-N-cyclopropylmethylbenzamide (370 mg; 1 mmol) and Pd/C 10%/H2 (60 mg/3 bar) in 60 mL THF. Yield: quantitative; MS: [M+H]+=342; HPLC: Rt=1.68 min (Method MC-6)

Sources & evidence

ORD record
ord-e2e561ec8ee94e03ba7be0473e177f77
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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