Triethylamine → HCID 86675792, compound

HRID 239901Notes

Reaction equation

HRID 239901 reaction equation
[Br:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([NH:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13]([CH2:19][OH:20])=[CH:12]3)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C>CS(C)=O>[Br:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([NH:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13]([CH:19]=[O:20])=[CH:12]3)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 70967971HCID 70967971, compound

Product 1

HCID 86675792HCID 86675792, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-bromo-N-[2-(hydroxymethyl)-1-methyl-1H-indol-5-yl]benzamide (13.63 g) obtained in Example 20 in DMSO (136 mL) were added triethylamine (21.1 mL) and pyridine-sulfur trioxide complex (24.16 g), and the mixture was stirred at room temperature for 22 hr. The reaction mixture was poured into ice water (400 mL), and the precipitated crystals were collected by filtration, washed with water, and dried to give the title compound (12.49 g, yield 92%) as a pale-brown solid. The solid was used without purification for the next reaction.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-e150ce9d16e74e37adb7b841e6fe3034
Source dataset
uspto-grants-2014_02
Patent number
US08642770B2

Reaction notes

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