2,6-Lutidine → 2-(1,3-benzodioxol-5-yl)-2-(5-bromo-1-methyl-1H-3-indolyl)acetic acid

HRID 850641Notes

Reaction equation

HRID 850641 reaction equation
CC1C=CC=C(C)N=1.[O:9]1[C:13]2[CH:14]=[CH:15][C:16]([CH:18](Br)[C:19]([O:21]C)=[O:20])=[CH:17][C:12]=2[O:11][CH2:10]1.[Br:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([CH3:34])[CH:29]=[CH:28]2>CN(C)C=O>[O:9]1[C:13]2[CH:14]=[CH:15][C:16]([CH:18]([C:28]3[C:27]4[C:31](=[CH:32][CH:33]=[C:25]([Br:24])[CH:26]=4)[N:30]([CH3:34])[CH:29]=3)[C:19]([OH:21])=[O:20])=[CH:17][C:12]=2[O:11][CH2:10]1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 2857575-Bromo-1-methyl-1H-indoleHCID 11821769Methyl 2-(1,3-benzodioxol-5-yl)-2-bromoacetate

Product 1

HCID 224672612-(1,3-benzodioxol-5-yl)-2-(5-bromo-1-methyl-1H-3-indolyl)acetic acidYield 79.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2,6-Dimethylpyridine (0.75 ml) was added to a stirred solution of methyl 2-(1,3-benzodioxol-5-yl)-2-bromoacetate (from Example 61(c), 1.75 g, 6.43 mmol) and 5-bromo-1-methylindole (from step (a), 1.35 g) in anhydrous dimethylformamide (10 ml) at ambient temperature, under a nitrogen atmosphere. The solution was heated to 80° C. for 8 hours. The reaction mixture was partitioned between diethylether and water, separated and the organic layer dried (magnesium sulphate) and evaporated in vacuo. The residue was flash chromatographed (using 50% dichloromethane and 50% hexane as eluant) to give the subtitle compound as a colourless oil (1.98 g).

Workup

  1. customThe reaction mixture was partitioned between diethylether and water
  2. customseparated
  3. dry with materialthe organic layer dried (magnesium sulphate)
  4. customevaporated in vacuo
  5. customchromatographed (using 50% dichloromethane and 50% hexane as eluant)

Sources & evidence

ORD record
ord-0ac0ddc957174f519d78662b43e54f88
Source dataset
uspto-grants-2000_01
Patent number
US06017945

Reaction notes

Loading…