1-Bromopentane → 7-fluoro-{[5-(trifluoromethyl)-2-furyl]methyl}-1H-indole-2,3-dione

HRID 545797Notes

Reaction equation

BrC1C=CC=C2C=1C=CN2.[F:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][C:18](=[O:21])[C:17]2=[O:22].BrCCCCC.Br[CH2:30][C:31]1[O:32][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:35]=1>>[F:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[N:19]([CH2:30][C:31]1[O:32][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:35]=1)[C:18](=[O:21])[C:17]2=[O:22]

Participants

Reactant 4

HCID 80571-Bromopentane

HCID 5864187-Fluoroisatin

HCID 6764944-Bromoindole

HCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furan

Product 1

HCID 666425707-fluoro-{[5-(trifluoromethyl)-2-furyl]methyl}-1H-indole-2,3-dione

Procedure

Following the procedure as described in PREPARATION 1A, and making non-critical variations to replace 4-bromoindole with 7-fluoroisatin, and 1-bromopentane with 2-(bromomethyl)-5-(trifluoromethyl)furan, the title compound was obtained (34%): MS (ES+) m/z 336.2 (M+23).

Sources & evidence

ORD record: ord-fa4561112a324eaaa5cd44454e739f7d
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935721B2

Reaction notes

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