1-Bromopentane → HCID 59263431, compound

HRID 425737Notes

Reaction equation

HRID 425737 reaction equation
[O:1]=[C:2]1[C:10]2([C:14]3[CH:15]=[C:16]([CH:19]4[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20]4)[CH:17]=[CH:18][C:13]=3[O:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.BrC1C=CC=C2C=1C=CN2.Br[CH2:43][C:44]1[O:45][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:47][CH:48]=1.BrCCCCC>>[O:1]=[C:2]1[C:10]2([C:14]3[CH:15]=[C:16]([CH:19]4[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20]4)[CH:17]=[CH:18][C:13]=3[O:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:43][C:44]1[O:45][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:47][CH:48]=1

Participants

5

Reactant 4

HCID 80571-BromopentaneHCID 6764944-BromoindoleHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 59263435HCID 59263435, compound

Product 1

HCID 59263431HCID 59263431, compound

Procedure

Following the procedure as described in PREPARATION 1A, and making non-critical variations using tert-butyl 3-(2′-oxo-1′,2′-dihydrospiro[1-benzofuran-3,3′-indol]-5-yl)piperidine-1-carboxylate to replace 4-bromoindole, and 2-(bromomethyl)-5-(trifluoromethyl)furan to replace 1-bromopentane, the title compound was obtained (10%) as a white solid: mp 59-61° C.; 1H NMR (300 MHz, CDCl3) δ 7.34-7.23 (m, 2H), 7.12 (d, 1H), 7.04-6.96 (m, 2H), 6.89 (d, 1H), 6.75 (s, 1H), 6.50 (s, 1H), 6.41 (s, 1H), 5.10-4.86 (m, 3H), 4.66 (d, 1H), 4.16-3.94 (m, 2H), 2.68-2.38 (m, 2H), 1.90-1.60 (m, 3H), 1.40 (s, 10H), 1.27-1.21 (m, 1H); MS (ES+) m/z 591.2 (M+23).

Sources & evidence

ORD record
ord-1b283a26def146dcb443c54bcade1075
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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