4-Chloroisatin → 1-(diphenylmethyl)-6-fluoro-1H-indole-2,3-dione

HRID 1407388Notes

Reaction equation

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

Participants

Reactant 2

HCID 960474-Chloroisatin

HCID 3739056-Fluoroisatin

Product 1

HCID 673578121-(diphenylmethyl)-6-fluoro-1H-indole-2,3-dione

Procedure

Following the procedure as described in PREPARATION 4A, and making non-critical variations using 6-fluoroisatin (Sadler, P. W., J. Org. Chem. (1956), 21(2):169-70) to replace 4-chloroisatin, 1-(diphenylmethyl)-6-fluoro-1H-indole-2,3-dione was obtained (76%): mp 167-169° C. (diethyl ether); 1H NMR (300 MHz, DMSO-d6) δ 7.41-7.27 (m, 11H), 6.77 (s, 1H), 6.30-6.26 (m, 1H), 5.82-5.80 (m, 1H); MS (ES+) m/z 354.1 (M+23).

Sources & evidence

ORD record: ord-6a8f29e0f6d647c09c2228bf8aa72954
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916580B2

Reaction notes

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