Hydrogen Bromide → Eletriptan Hydrobromide

HRID 584854Notes

Reaction equation

[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][CH2:18][S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:15]=2)[NH:10][CH:9]=1.[BrH:28]>CC(C)=O>[BrH:28].[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][CH2:18][S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:20])=[O:21])[CH:15]=2)[NH:10][CH:9]=1

Participants

Conditions

Temperature: 32.5 °C

Procedure

3-{[1-Methylpyrrolidin-2(R)-yl]methyl}-5-(2-phenylsulphonylethyl)-1H-indole (274 kg) and acetone (3419 kg) were charged to a dry, glass-lined vessel. A solution of 48% aqueous hydrobromic acid (114.7 kg) in acetone (1383 kg) was added at a temperature of from 50 to 55° C. over 1 hour and the resulting slurry was stirred for 4 hours. The reaction mixture was cooled to from 30 to 35° C. and the product was isolated by filtration. The product was washed with acetone (861 kg) to yield the α-polymorphic form of 3-{[1-methylpyrrolidin-2(R)-yl]methyl}-5-(2-phenylsulphonylethyl)-1H-indole hydrobromide (242.4 kg dry, 73.0%).

Workup

customthe product was isolated by filtration
washThe product was washed with acetone (861 kg)

Sources & evidence

ORD record: ord-4521c868405b42fcab8a01dc688fce4d
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06927296B2

Reaction notes

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