Triethylamine → HCID 58834661, compound

HRID 1443824Notes

Reaction equation

HRID 1443824 reaction equation
CS(Cl)(=O)=O.O[CH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[CH:18][NH:19]2)=[C:15]([Br:22])[CH:14]=1)=[O:12].C(N(CC)CC)C.[NH:30]1[CH2:34][CH2:33][CH2:32][C@H:31]1[CH2:35][OH:36]>C1COCC1>[OH:36][CH2:35][C@@H:31]1[CH2:32][CH2:33][CH2:34][N:30]1[CH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[CH:18][NH:19]2)=[C:15]([Br:22])[CH:14]=1)=[O:12]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 640091L-ProlinolHCID 58834671HCID 58834671, compound

Product 1

HCID 58834661HCID 58834661, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution methanesulfonyl chloride (0.13 mL, 1.68 mmol) in THF (1 mL) was added to a solution of 4-bromo-1H-indole-6-carboxylic acid (3-hydroxy-propyl)-amide (0.50 g, 1.68 mmol) and triethylamine (0.25 mL, 1.84 mmol) in tetrahydrofuran (5 mL) at 0° C. and slowly warmed to room temperature over 30 minutes. (S)-(+)-2-pyrrolidinemethanol (1.0 g, 9.88 mmol) was added and stirred at room temperature overnight. The reaction was concentrated in vacuo and purified by column chromatography (5% methanol in dichloromethane) to yield 0.50 g (78%) of (S)-4-bromo-1H-indole-6-carboxylic acid [3-(2-hydroxymethyl-pyrrolidin-1-yl)-propyl]-amide. Mass spectrum (LCMS, ESI pos.): Calcd for C17H22BrN3O2 379.09. Found 380.0; (M+H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by column chromatography (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a7f4f458bdab4e84a6cb6bef19a151ce
Source dataset
uspto-grants-2010_02
Patent number
US07662824B2

Reaction notes

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