1'-(diphenylmethyl)-3-methylspiro[furo[2,3-f][1,3]benzoxazole-7,3'-indole]-2,2'(1'H,3H)-dione → 3-methylspiro[furo[2,3-f][1,3]benzoxazole-7,3'-indole]-2,2'(1H,3H)-dione
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]5[O:26][C:25](=[O:27])[N:24]([CH3:28])[C:23]=5[CH:29]=[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>>[CH3:28][N:24]1[C:23]2[CH:29]=[C:19]3[O:18][CH2:17][C:10]4([C:11]5[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=5)[NH:8][C:9]4=[O:30])[C:20]3=[CH:21][C:22]=2[O:26][C:25]1=[O:27]Participants
Reactant 2
Product 1
Procedure
Following the procedure as described in EXAMPLE 3 and making non-critical variations using 1′-(diphenylmethyl)-3-methylspiro[furo[2,3-f][1,3]benzoxazole-7,3′-indole]-2,2′(1′H,3H)-dione to replace 1′-(diphenylmethyl)-6-methoxy-5-methylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one, 3-methylspiro[furo[2,3-f][1,3]benzoxazole-7,3′-indole]-2,2′(1′H,3H)-dione was obtained (88%) as a colorless solid: mp>250° C. (diethyl ether); 1H NMR (300 MHz, DMSO-d6) δ10.64 (br s, 1H), 7.30-7.22 (m, 1H), 7.09 (d, J=7.0 Hz, 1H), 7.01-6.90 (m, 3H), 6.75 (s, 1H), 4.82 (d, J=9.3 Hz, 1H), 4.70 (d, J=9.3 Hz, 1H), 3.30 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ178.2, 157.0, 154.5, 141.8, 136.2, 132.8, 132.4, 128.9, 123.8, 122.3, 122.0, 109.9, 104.9, 92.3, 79.8, 57.8, 28.2; MS (ES+) m/z 309.1 (M+1).
Sources & evidence
- ORD record
- ord-191f75a771a14d48b4a375031df25db8
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263606B2
Reaction notes
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