Diisopropylethylamine → 2-(5-bromo-7-fluoro-4-methoxy-1H-indol-3-yl)-N,N-dimethylacetamide

HRID 1404090Notes

Reaction equation

HRID 1404090 reaction equation
[Br:1][C:2]1[C:3]([O:16][CH3:17])=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:12][C:13](O)=[O:14].[CH3:18][N:19](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:20].F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1>[Br:1][C:2]1[C:3]([O:16][CH3:17])=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:12][C:13]([N:19]([CH3:20])[CH3:18])=[O:14]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 669271742-(5-bromo-7-fluoro-4-methoxy-1H-indol-3-yl)acetic acid

Product 1

HCID 669271532-(5-bromo-7-fluoro-4-methoxy-1H-indol-3-yl)-N,N-dimethylacetamideYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 8-9 (11.5 g, 38.0 mmol) in THF (300 mL) was added HATU (22.0 g, 58.0 mmol) Me2NH.HCl (3.1 g, 38.0 mmol) at 0° C. After the mixture was stirred for 5 minutes, DIPEA (12.3 g, 95.3 mmol) was added. The mixture was stirred overnight at room temperature. The volatile was removed and the residue was purified by flash chromatography (Silica gel, DCM/MeOH=50:1) to afford 8-10 (9.0 g, 72%) as white solid.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. customThe volatile was removed
  3. customthe residue was purified by flash chromatography (Silica gel, DCM/MeOH=50:1)

Sources & evidence

ORD record
ord-87d18db9cf894eb8ade78e0fa66ee0c8
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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