2,6-Lutidine → Methyl 2-(1,3-benzodioxol-5-yl)-2-[6-(hydroxymethyl)1-methyl-1H-3-indolyl]acetate

HRID 381322Notes

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][CH3:22])=[O:20])=[CH:17][C:12]=2[O:11][CH2:10]1.[OH:24][CH2:25][C:26]1[CH:34]=[C:33]2[C:29]([CH:30]=[CH:31][N:32]2[CH3:35])=[CH:28][CH:27]=1>CN(C)C=O>[O:9]1[C:13]2[CH:14]=[CH:15][C:16]([CH:18]([C:30]3[C:29]4[C:33](=[CH:34][C:26]([CH2:25][OH:24])=[CH:27][CH:28]=4)[N:32]([CH3:35])[CH:31]=3)[C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:12]=2[O:11][CH2:10]1

Participants

Conditions

Temperature: 80 °C

Procedure

2,6-Dimethylpyridine (0.12 ml) was added to a stirred solution of methyl 2-(1,3-benzodioxol-5-yl)-2-bromoacetate (from step (c), 273 mg, 1 mmol) and 6-(hydroxymethyl)-1-methylindole (from step (a), 161 mg, 1 mmol) in anhydrous dimethylformamide (2 ml) at ambient temperature, under a nitrogen atmosphere. The solution was heated to 80° C. for 3 hours. The reaction mixture was cooled, and partitioned between diethylether and water, separated and the organic layer dried (magnesium sulphate) and evaporated in vacuo. The residue was flash chromatographed (using diethyl ether as eluant) to give the subtitle compound as a colourless foam (273 mg).

Workup

temperatureThe reaction mixture was cooled
custompartitioned between diethylether and water
customseparated
dry with materialthe organic layer dried (magnesium sulphate)
customevaporated in vacuo
customchromatographed (using diethyl ether as eluant)

Sources & evidence

ORD record: ord-fcc4fb89d75d4e3cbdeaea3369946b4e
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06306852B1

Reaction notes

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