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

HRID 1407642Notes

Reaction equation

HRID 1407642 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]([O:25][CH2:26][CH2:27][O:28][CH3:29])[CH:23]=[CH:24][C:19]=4[O:18][CH2:17]3)[C:9]2=[O:30])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>>[CH3:29][O:28][CH2:27][CH2:26][O: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:30])[C:20]=2[CH:21]=1

Participants

3

Reactant 2

HCID 593522991'-(diphenylmethyl)-5-(2-methoxyethoxy)spiro[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 593525575-(2-methoxyethoxy)spiro[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-(2-methoxyethoxy)spiro[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-(2-methoxyethoxy)spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one was obtained (30%): 1H NMR (300 MHz, CDCl3) δ8.38 (s, 1H), 7.24-7.18 (m, 1H), 7.15-7.07 (m, 1H), 7.06-6.97 (m, 1H), 6.96-6.88 (m, 1H), 6.70-6.61 (m, 1H), 6.54 (s, 1H), 6.43-6.35 (m, 1H), 4.82 (ABq, 2H), 4.13-3.98 (m, 2H), 3.75-3.67 (m, 2H), 3.42 (s, 1H).

Sources & evidence

ORD record
ord-ae22ca05d3bb47c7a29675e54dd4f69e
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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