Water → HCID 19870652, compound

HRID 330145Notes

Reaction equation

HRID 330145 reaction equation
[CH:1]1([CH2:6][NH:7][C:8](=[O:21])[CH2:9][C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH:19]=[O:20])=[CH:15][NH:16]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:23][C:24]1[CH:36]=[CH:35][C:27]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:26][C:25]=1[O:37][CH3:38].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:1]1([CH2:6][NH:7][C:8]([CH2:9][C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH:19]=[O:20])=[CH:15][N:16]3[CH2:23][C:24]3[CH:36]=[CH:35][C:27]([C:28]([O:30][C:31]([CH3:34])([CH3:32])[CH3:33])=[O:29])=[CH:26][C:25]=3[O:37][CH3:38])=[CH:12][CH:11]=2)=[O:21])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 14523519Tert-butyl 4-(bromomethyl)-3-methoxybenzoateHCID 53983395N-cyclopentylmethyl-3-formylindole-6-acetamide

Product 1

HCID 19870652HCID 19870652, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-cyclopentylmethyl-3-formylindole-6-acetamide (0.52 g), t-butyl 4-bromomethyl-3-methoxybenzoate (0.66 g), and potassium carbonate (0.37 g) in N,N-dimethylformamide (10 ml) was stirred for 48 hr under a nitrogen atmosphere. Water was added to give a precipitate which was collected by filtration and purified by flash chromatography, eluting with 1:49 methanol:chloroform, to give t-butyl 4-[6-(cyclopentylmethylcarbamoyl)methyl-3-formylindol-1-ylmethyl]-3-methoxybenzoate (0.90 g, 97%) as a white solid; partial NMR (80 MHz, CDCl3): 1.56 (s, 9H, C(CH3)3), 3.09(t, 2H, NHCH2), 3.65(s, 2H, COCH2), 3.93(s, 3H, OCH3), 9.98(s, 1H, CHO).

Workup

  1. customto give a precipitate which
  2. filtrationwas collected by filtration
  3. custompurified by flash chromatography
  4. washeluting with 1:49 methanol

Sources & evidence

ORD record
ord-f8be24e6b47d4dbfa5400281ce81a3e1
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

Loading…