1-(diphenylmethyl)-5',6',7',8'-tetrahydrospiro[indole-3,3'-naphtho[2,3-b]furan]-2(1'H)-one → 5',6',7',8'-tetrahydrospiro[indole-3,3'-naphtho[2,3-b]furan]-2(1H)-one

HRID 1407640Notes

Reaction equation

HRID 1407640 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:10]3([CH2:14][O:13][C:12]4[CH:15]=[C:16]5[C:21](=[CH:22][C:11]3=4)[CH2:20][CH2:19][CH2:18][CH2:17]5)[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>>[O:13]1[CH2:14][C:10]2([C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[NH:8][C:9]2=[O:29])[C:11]2[CH:22]=[C:21]3[C:16](=[CH:15][C:12]1=2)[CH2:17][CH2:18][CH2:19][CH2:20]3

Participants

3

Reactant 2

HCID 461954301-(diphenylmethyl)-5',6',7',8'-tetrahydrospiro[indole-3,3'-naphtho[2,3-b]furan]-2(1'H)-oneHCID 593524081'-(diphenylmethyl)-6-methoxy-5-methylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

Product 1

HCID 461954285',6',7',8'-tetrahydrospiro[indole-3,3'-naphtho[2,3-b]furan]-2(1H)-one

Procedure

Following the procedure as described in EXAMPLE 3 and making non-critical variations using 1-(diphenylmethyl)-5′,6′,7′,8′-tetrahydrospiro[indole-3,3′-naphtho[2,3-b]furan]-2(1′H)-one to replace 1′-(diphenylmethyl)-6-methoxy-5-methylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one, 5′,6′,7′,8′-tetrahydrospiro[indole-3,3′-naphtho[2,3-b]furan]-2(1′H)-one was obtained (80%) as a colorless solid: mp>230° C.; 1H NMR (300 MHz, CDCl3) δ 8.13 (s, 1H), 7.33-7.19 (m, 1H), 7.16 (d, J=7.4 Hz, 1H), 7.04 (dd, J=7.5, 7.5 Hz, 1H), 6.95 (d, J=7.7 Hz, 1H), 6.68 (s, 1H), 6.49 (s, 1H), 4.92 (d, J=9.0 Hz, 1H), 4.65 (d, J=9.0 Hz, 1H), 2.76-2.72 (m, 2H), 2.58-2.56 (m, 2H), 1.71 (t, J=3.2 Hz, 4H); 13C NMR (75 MHz, CDCl3) δ180.5, 158.7, 140.4, 139.0, 132.9, 130.2, 128.8, 126.0, 124.1, 123.6, 123.3, 110.3, 110.2, 79.6, 58.6, 30.0, 29.0, 23.2, 23.0; MS (ES+) m/z 292.0 (M+1).

Sources & evidence

ORD record
ord-25340e5478b048eaa015b044f8504921
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

Loading…