1'-(diphenylmethyl)-6-methoxy-5-methylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one → 7H-spiro[furo[2,3-g]quinoxaline-8,3'-indolin]-2'-one

HRID 1965501Notes

Reaction equation

HRID 1965501 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:28]4[CH:27]=[C:26]5[C:21]([N:22]=[CH:23][CH:24]=[N:25]5)=[CH:20][C:19]=4[O:18][CH2:17]3)[C:9]2=[O:29])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>>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2([C:28]3[CH:27]=[C:26]4[C:21]([N:22]=[CH:23][CH:24]=[N:25]4)=[CH:20][C:19]=3[O:18][CH2:17]2)[C:9]1=[O:29]

Participants

3

Reactant 2

HCID 593524081'-(diphenylmethyl)-6-methoxy-5-methylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneHCID 593527301'-(diphenylmethyl)spiro[furo[2,3-g]quinoxaline-8,3'-indol]-2'(1'H)-one

Product 1

HCID 593522117H-spiro[furo[2,3-g]quinoxaline-8,3'-indolin]-2'-one

Procedure

Following the procedure as described in EXAMPLE 3 and making non-critical variations using 1′-(diphenylmethyl)spiro[furo[2,3-g]quinoxaline-8,3′-indol]-2′(1′H)-one to replace 1′-(diphenylmethyl)-6-methoxy-5-methylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one, spiro[furo[2,3-g]quinoxaline-8,3′-indol]-2′(1′H)-one was obtained (22%): mp 206-207° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 10.78 (s, 1H), 8.68-8.61 (m, 2H), 8.06 (d, J=9.0 Hz, 1H), 7.68 (d, J=9.0 Hz, 1H), 7.21-7.18 (m, 1H), 7.03-6.86 (m, 3H), 6.96 (ABq, 2H); MS (ES+) m/z 289.8 (M+1).

Sources & evidence

ORD record
ord-e63a58f536bd4e07b33288bcb2dacd4b
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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