4-Chloroisatin → 1-(diphenylmethyl)-7-fluoro-1H-indole-2,3-dione

HRID 2384995Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[C:7]2=[O:12].Cl[C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[C:16](=O)[C:17](=O)N2>>[C:15]1([CH:16]([C:17]2[CH:4]=[CH:3][CH:2]=[CH:10][CH:6]=2)[N:9]2[C:10]3[C:6](=[CH:5][CH:4]=[CH:3][C:2]=3[F:1])[C:7](=[O:12])[C:8]2=[O:11])[CH:19]=[CH:20][CH:21]=[CH:22][CH:14]=1

Participants

Reactant 2

HCID 960474-Chloroisatin

HCID 5864187-Fluoroisatin

Product 1

HCID 673566781-(diphenylmethyl)-7-fluoro-1H-indole-2,3-dione

Procedure

Following the procedure as described in PREPARATION 4A, and making non-critical variations using 7-fluoro-1H-indole-2,3-dione (Kalia, N., et al., J. Med. Chem. 2007; 50:21-39) to replace 4-chloro-1H-indole-2,3-dione, 1-(diphenylmethyl)-7-fluoro-1H-indole-2,3-dione was obtained (56%) as an orange solid: 1H NMR (300 MHz, CDCl3) δ7.52-7.47 (m, 1H), 7.42-7.30 (m, 10H), 7.29-7.21 (m, 1H), 7.13-7.05 (m, 1H), 6.99 (br s, 1H); MS (ES+) m/z 353.9 (M+23).

Sources & evidence

ORD record: ord-5f9233201e4446dfb42a0cd35536275c
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263606B2

Reaction notes

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