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

HRID 1965359Notes

Reaction equation

HRID 1965359 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.[C:23]1([CH:29]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[N:30]2[C:38]3[C:33](=[C:34]([F:39])[CH:35]=[CH:36][CH:37]=3)[C:32](=[O:40])[C:31]2=[O:41])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N1C2C(=CC=CC=2)C(=O)C1=O>>[C:42]1([CH:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:30]2[C:38]3[C:33](=[C:34]([F:39])[CH:35]=[CH:36][CH:37]=3)[C:32]([OH:40])([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:41])[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

5

Reactant 4

HCID 7054IsatinHCID 6997992-Methyl-1,3-benzothiazol-5-olHCID 91152732,3-Dihydro-1,4-benzodioxin-6-olHCID 685968111-(diphenylmethyl)-4-fluoro-1H-indole-2,3-dione

Product 1

HCID 673584151-(diphenylmethyl)-4-fluoro-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-(diphenylmethyl)-4-fluoro-1H-indole-2,3-dione to replace isatin, 1-(diphenylmethyl)-4-fluoro-3-hydroxy-3-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-dihydro-2H-indol-2-one was obtained (83%) as a colourless solid: mp 209-211° C. (dec.); 1H NMR (300 MHz, DMSO-d6) δ 9.15 (s, 1H), 7.43-7.27 (m, 11H), 7.01 (ddd, J=8.2, 8.2, 5.9 Hz, 1H), 6.87 (s, 1H), 6.79 (s, 1H), 6.61 (dd, J=8.8, 8.8 Hz, 1H), 6.21 (s, 1H), 6.16 (d, J=7.9 Hz, 1H), 4.25-4.14 (m, 4H); 13C NMR (75 MHz, DMSO-d6) δ 176.2, 157.9 (d, 1JC-F=248 Hz), 147.1, 145.0 (d, 3JC-F=8.7 Hz), 142.7, 137.7 (d, 2JC-F=30.9 Hz), 135.4, 130.1 (d, 3JC-F=8.7 Hz), 128.4 (d, 3JC-F=13.9 Hz), 128.3 (d, 3JC-F=8.4 Hz), 127.5 (d, 3JC-F=11.9 Hz), 119.4, 117.9 (d, 2JC-F=18.9 Hz), 116.1, 109.3 (d, 2JC-F=20.3 Hz), 107.2 (d, 4JC-F=2.1 Hz), 103.1, 73.0, 64.2, 63.7, 57.5; MS (ES+) m/z 506.0 (M+23).

Sources & evidence

ORD record
ord-a39fe85c55a446bd9f24512ca3416091
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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