1'-(diphenylmethyl)-5-hydroxyspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one → 5-hydroxyspiro[1-benzofuran-3,3'-indol]-2'(1'H)one

HRID 425732Notes

Reaction equation

HRID 425732 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3([C:20]4[CH:21]=[C:22]([OH:25])[CH:23]=[CH:24][C:19]=4[O:18][CH2:17]3)[C:9]2=[O:26])C=CC=CC=1.C1(C(C2C=CC=CC=2)N2C3C(=CC(C)=CC=3)C3(C4=CC5OCOC=5C=C4OC3)C2=O)C=CC=CC=1>>[OH:25][C:22]1[CH:23]=[CH:24][C:19]2[O:18][CH2:17][C:10]3([C:11]4[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=4)[NH:8][C:9]3=[O:26])[C:20]=2[CH:21]=1

Participants

3

Reactant 2

HCID 592634041'-(diphenylmethyl)-5-hydroxyspiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneHCID 59263474(diphenylmethyl)-5'-methylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

Product 1

HCID 592634445-hydroxyspiro[1-benzofuran-3,3'-indol]-2'(1'H)one

Procedure

Following the procedure as described in EXAMPLE 1.28, and making non-critical variations using 1′-(diphenylmethyl)-5-hydroxyspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one to replace 1′-(diphenylmethyl)-5′-methylspiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one, the title compound was obtained (48%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 10.58 (s, 1H), 8.85 (s, 1H), 7.21 (dt, 1H), 7.06 (d, 1H), 6.94 (dd, 1H), 6.89 (d, 1H), 6.72 (d, 1H), 6.54 (dd, 1H), 6.02 (d, 1H), 4.70 (d, 1H), 4.57 (d, 1H); MS (ES+) m/z 254.2 (M+1).

Sources & evidence

ORD record
ord-ed5d265e4605431c981c0b5781936b95
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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