Isatin → 1-(4-fluorophenyl)-3-hydroxy-3-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-dihydro-2H-indol-2-one

HRID 2385092Notes

Reaction equation

HRID 2385092 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:2]1=2.CC1SC2C=CC(O)=CC=2N=1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32](=[O:39])[C:31]2=[O:40])=[CH:26][CH:25]=1.N1C2C(=CC=CC=2)C(=O)C1=O>>[F:23][C:24]1[CH:25]=[CH:26][C:27]([N:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]([OH:39])([C:9]3[C:8]([OH:11])=[CH:7][C:3]4[O:4][CH2:5][CH2:6][O:1][C:2]=4[CH:10]=3)[C:31]2=[O:40])=[CH:28][CH:29]=1

Participants

5

Reactant 4

HCID 7054IsatinHCID 6997992-Methyl-1,3-benzothiazol-5-olHCID 91152732,3-Dihydro-1,4-benzodioxin-6-olHCID 139250931-(4-Fluorophenyl)indoline-2,3-dione

Product 1

HCID 673562561-(4-fluorophenyl)-3-hydroxy-3-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 1A and making non-critical variations using 2,3-dihydrobenzo[b][1,4]dioxin-6-ol to replace 2-methylbenzo[d]thiazol-5-ol, and 1-(4-fluorophenyl)indoline-2,3-dione (Coppola, G. M Journal of Heterocyclic Chemistry 1987, (24):1249) to replace isatin, 1-(4-fluorophenyl)-3-hydroxy-3-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-dihydro-2H-indol-2-one was obtained (23%) as a beige solid: mp 195-200° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.12 (s, 1H), 7.47-7.41 (m, 4H), 7.26 (s, 1H), 7.21-7.16 (m, 1H), 7.01-6.93 (m, 2H), 6.68 (d, J=7.8 Hz, 1H), 6.63 (s, 1H), 6.14 (s, 1H), 4.23-4.14 (m, 4H); 13C NMR (75 MHz, DMSO-d6) δ 176.3, 160.9 (d, 1JC-F=245 Hz), 147.1, 143.9, 142.6, 135.6, 132.0, 131.2 (d, 4JC-F=2.9 Hz), 128.6 (d, 3JC-F=8 Hz), 124.0, 122.4, 121.2, 116.4 (d, 2JC-F=22.8 Hz), 115.1, 108.2, 103.4, 74.4, 64.3, 63.7, 57.2; MS (ES+) m/z 390.0 (M+1).

Sources & evidence

ORD record
ord-c1f1686145474dca93f9f5523fbdb4ff
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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