4-bromo-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one → 5-fluoro-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-{[5-(trifluoromethyl)-2-furyl]methyl}-1,3-dihydro-2H-indol-2-one

HRID 1259635Notes

Reaction equation

HRID 1259635 reaction equation
BrC1C=CC=C2C=1C(O)(C1C(O)=CC3OCOC=3C=1)C(=O)N2CCCCC.[F:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[N:34]([CH2:38][C:39]1[O:40][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:42][CH:43]=1)[C:33](=[O:48])[C:32]2(O)[C:49]1[C:57]([OH:58])=[CH:56][C:52]2[O:53][CH2:54][O:55][C:51]=2[CH:50]=1>>[F:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[N:34]([CH2:38][C:39]1[O:40][C:41]([C:44]([F:47])([F:45])[F:46])=[CH:42][CH:43]=1)[C:33](=[O:48])[CH:32]2[C:49]1[C:57]([OH:58])=[CH:56][C:52]2[O:53][CH2:54][O:55][C:51]=2[CH:50]=1

Participants

3

Reactant 2

HCID 120044004-bromo-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-oneHCID 588725415-fluoro-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-{[5-(trifluoromethyl)-2-furyl]methyl}-1,3-dihydro-2H-indol-2-one

Product 1

HCID 588725305-fluoro-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-{[5-(trifluoromethyl)-2-furyl]methyl}-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 1D, and making non-critical variations to replace 4-bromo-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one with 5-fluoro-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-{[5-(trifluoromethyl)-2-furyl]methyl}-1,3-dihydro-2H-indol-2-one, the title compound was obtained (72%) as a pale yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 9.31 (s, 1H), 7.13 (dd, 1H), 7.02 (dd, 2H), 6.82 (d, 1H), 6.59 (d, 2H), 6.39 (s, 1H), 5.87 (d, 2H), 5.07-4.96 (m, 2H), 4.84 (s, 1H); 13C NMR (75 MHz, DMSO-d6) δ 176.1, 160.5, 157.4, 153.9, 150.5, 147.5, 140.2, 139.6, 139.1, 132.3 (d, 2JCF=33.3 Hz), 115.3, 114.5 (m), 114.2, 113.9, 111.9 (d, 1JCF=98.7 Hz), 109.9, 109.7 (d, 2JCF=32.7 Hz), 101.3, 98.3, 48.5, 36.8; MS (ES+) m/z 436.2 (M+1).

Sources & evidence

ORD record
ord-a20ff5b3ca5943d1aaa04dbaa6f88f44
Source dataset
uspto-grants-2013_06
Patent number
US08466188B2

Reaction notes

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