3-(2,2-difluoro-6-hydroxy-1,3-benzodioxol-5-yl)-3-hydroxy-1-{[5-(trifluoromethyl)furan-2-yl]methyl}-1,3-dihydro-2H-indol-2-one → 3-(2,2-difluoro-6-hydroxy-1,3-benzodioxol-5-yl)-1-methyl-1,3-dihydro-2H-indol-2-one

HRID 2385065Notes

Reaction equation

HRID 2385065 reaction equation
[F:1][C:2]1([F:26])[O:6][C:5]2[CH:7]=[C:8]([OH:25])[C:9]([C:11]3(O)[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]([CH2:20]OC)[C:12]3=[O:23])=[CH:10][C:4]=2[O:3]1.FC1(F)OC2C=C(O)C(C3(O)C4C(=CC=CC=4)N(CC4OC(C(F)(F)F)=CC=4)C3=O)=CC=2O1>>[F:26][C:2]1([F:1])[O:6][C:5]2[CH:7]=[C:8]([OH:25])[C:9]([CH:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]([CH3:20])[C:12]3=[O:23])=[CH:10][C:4]=2[O:3]1

Participants

3

Reactant 2

HCID 673577963-(2,2-difluoro-6-hydroxy-1,3-benzodioxol-5-yl)-3-hydroxy-1-{[5-(trifluoromethyl)furan-2-yl]methyl}-1,3-dihydro-2H-indol-2-oneHCID 685998533-(2,2-difluoro-6-hydroxy-1,3-benzodioxol-5-yl)-3-hydroxy-1-(methoxymethyl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 673578903-(2,2-difluoro-6-hydroxy-1,3-benzodioxol-5-yl)-1-methyl-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 71B and making non-critical variations using 3-(2,2-difluoro-6-hydroxy-1,3-benzodioxol-5-yl)-3-hydroxy-1-(methoxymethyl)-1,3-dihydro-2H-indol-2-one to replace 3-(2,2-difluoro-6-hydroxy-1,3-benzodioxol-5-yl)-3-hydroxy-1-{[5-(trifluoromethyl)furan-2-yl]methyl}-1,3-dihydro-2H-indol-2-one, 3-(2,2-difluoro-6-hydroxy-1,3-benzodioxol-5-yl)-1-methyl-1,3-dihydro-2H-indol-2-one was obtained (85%) as a colorless amorphous solid: 1H NMR (300 MHz, CDCl3) δ7.47-7.40 (m, 1H), 7.37-7.31 (m, 1H), 7.28-7.20 (m, 2H), 6.99 (d, J=7.8 Hz, 1H), 6.85 (s, 1H), 6.60 (s, 1H), 5.10 (s, 1H), 3.25 (s, 3H); MS (ES+) m/z 320.1 (M+1).

Sources & evidence

ORD record
ord-7fdfd0d510354636b9770d99e872e664
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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