Isatin → 5-fluoro-1-{[5-(trifluoromethyl)-2-furyl]methyl}-1H-indole-2,3-dione

HRID 1259634Notes

Reaction equation

HRID 1259634 reaction equation
N1C2C(=CC=CC=2)C(=O)C1=O.[F:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])[C:16]2=[O:23].BrCCC1CC1.Br[CH2:31][C:32]1[O:33][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:35][CH:36]=1>>[F:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([CH2:31][C:32]1[O:33][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:35][CH:36]=1)[C:17](=[O:22])[C:16]2=[O:23]

Participants

5

Reactant 4

HCID 7054IsatinHCID 2365665-FluoroisatinHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 22636989(2-Bromoethyl)cyclopropane

Product 1

HCID 666424895-fluoro-1-{[5-(trifluoromethyl)-2-furyl]methyl}-1H-indole-2,3-dione

Procedure

Following the procedure as described in PREPARATION 2A, and making non-critical variations to replace isatin with 5-fluoroisatin, and (2-bromoethyl)cyclopropane with 2-(bromomethyl)-5-(trifluoromethyl)furan, the title compound was obtained (59%) as a red solid: 1H NMR (300 MHz, DMSO-d6) δ 7.54-7.50 (m, 1H), 7.47-7.44 (m, 1H), 7.20 (dd, 1H), 7.14-7.13 (m, 1H), 6.75 (d, 1H), 4.99 (s, 2H); 13C NMR (75 MHz, DMSO-d6) δ 182.4 (d), 160.7, 158.5 (d), 157.5, 153.0 (d), 146.5 (d), 139.9 (q), 124.3, 119.3 (d), 114.5 (d), 112.7 (d), 112.0 (d), 110.5, 36.8.

Sources & evidence

ORD record
ord-1405b20bbf2f4782a06a17e311e8f006
Source dataset
uspto-grants-2013_06
Patent number
US08466188B2

Reaction notes

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