1'-(diphenylmethyl)-5,6-dimethylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one → 5,6-dimethylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 1965472Notes

Reaction equation

HRID 1965472 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]([CH3:26])[C:23]([CH3:25])=[CH:24][C:19]=4[O:18][CH2:17]3)[C:9]2=[O:27])C=CC=CC=1.C1(C(C2C=CC=CC=2)N2C3C(=CC=CC=3)C3(C4C=C(C)C(OC)=CC=4OC3)C2=O)C=CC=CC=1>>[CH3:26][C:22]1[C:23]([CH3:25])=[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:27])[C:20]=2[CH:21]=1

Participants

3

Reactant 2

HCID 461941831'-(diphenylmethyl)-5,6-dimethylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneHCID 593524081'-(diphenylmethyl)-6-methoxy-5-methylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

Product 1

HCID 461940495,6-dimethylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

Procedure

Following the procedure as described in EXAMPLE 3 and making non-critical variations using 1′-(diphenylmethyl)-5,6-dimethylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one to replace 1′-(diphenylmethyl)-6-methoxy-5-methylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one, 5,6-dimethylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one was obtained (88%) as a colorless solid: mp 206-207° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ10.5 (s, 1H), 7.23-7.18 (m, 1H), 7.03-7.01 (m, 1H), 6.94-6.88 (m, 2H), 6.73 (s, 1H), 6.43 (s, 1H), 4.68 (ABq, 2H), 2.13 (s, 3H), 1.99 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ178.9, 159.1, 142.2, 138.0, 133.3, 129.1, 127.0, 124.2, 124.1, 122.7, 111.2, 110.2, 79.5, 58.2, 20.2, 19.1; MS (ES+) m/z 266.3 (M+1).

Sources & evidence

ORD record
ord-8b7fd8038ff54e22aca2d8791e5c8208
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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