Triethylamine → 5-bromo-3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide

HRID 2267494Notes

Reaction equation

HRID 2267494 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[C:18]([C:29]([NH2:31])=[O:30])[CH:19]=[C:20](C4C=CC=CC=4)[CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1)(=[O:7])=[O:6].[Br:32]C1C=C2C(=C(C(N)=O)C=1)NC=C2C1CCNCC1.C(N(CC)CC)C.ClCCCS(Cl)(=O)=O>>[Br:32][C:20]1[CH:21]=[C:22]2[C:17](=[C:18]([C:29]([NH2:31])=[O:30])[CH:19]=1)[NH:16][CH:15]=[C:14]2[CH:11]1[CH2:12][CH2:13][N:8]([S:5]([CH2:4][CH2:3][CH2:2][Cl:1])(=[O:7])=[O:6])[CH2:9][CH2:10]1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 113247225-bromo-3-(4-piperidinyl)-1H-indole-7-carboxamideHCID 590032803-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide

Product 1

HCID 590033105-bromo-3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamideYield 52%

Procedure

The title compound was prepared according to the general procedure for intermediate 11. 5-bromo-3-(4-piperidinyl)-1H-indole-7-carboxamide (875 mg, 2.72 mmol) was reacted with triethyl amine (2.27 mL, 16.32 mmol) and 3-chloropropylsulfonyl chloride (0.64 mL, 5.44 mmol) to give the title compound (656 mg, 52%)

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-f24de586e08b4729a3fcc1a8dedc9369
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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