1-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-3-(4-methoxybenzyl)-1,3-dihydro-2H-pyrrolo[3,2-f]quinolin-2-one → 3'-(4-methoxybenzyl)-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,1'-pyrrolo[3,2-f]quinolin]-2'(3'H)-one

HRID 2385177Notes

Reaction equation

HRID 2385177 reaction equation
[OH:1][C:2]1[C:10]([CH:11]2[C:15]3=[C:16]4[C:21](=[CH:22][CH:23]=[C:14]3[N:13]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[C:12]2=[O:33])[N:20]=[CH:19][CH:18]=[CH:17]4)=[CH:9][C:5]2[CH2:6][CH2:7][O:8][C:4]=2[CH:3]=1.[C:34]1(C(C2C=CC=CC=2)N2C3C(=CC=CC=3)C(C3C=C(C)C(OC)=CC=3O)C2=O)C=CC=CC=1>>[CH3:32][O:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:13]2[C:14]3[C:15](=[C:16]4[C:21](=[CH:22][CH:23]=3)[N:20]=[CH:19][CH:18]=[CH:17]4)[C:11]3([CH2:34][O:1][C:2]4[CH:3]=[C:4]5[C:5](=[CH:9][C:10]3=4)[CH2:6][CH2:7][O:8]5)[C:12]2=[O:33])=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 673560781-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-3-(4-methoxybenzyl)-1,3-dihydro-2H-pyrrolo[3,2-f]quinolin-2-oneHCID 673563761-(diphenylmethyl)-3-(2-hydroxy-4-methoxy-5-methylphenyl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 593527073'-(4-methoxybenzyl)-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,1'-pyrrolo[3,2-f]quinolin]-2'(3'H)-one

Procedure

Following the procedure as described in EXAMPLE 2 and making non-critical variations using 1-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-3-(4-methoxybenzyl)-1,3-dihydro-2H-pyrrolo[3,2-f]quinolin-2-one to replace 1-(diphenylmethyl)-3-(2-hydroxy-4-methoxy-5-methylphenyl)-1,3-dihydro-2H-indol-2-one, 3′-(4-methoxybenzyl)-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,1′-pyrrolo[3,2-f]quinolin]-2′(3′H)-one was obtained (9%) as a yellow solid: mp 169-170° C.; 1H NMR (300 MHz, CDCl3) δ 8.75 (s, 1H), 8.10 (m, 1H), 7.92 (m, 1H), 7.43-7.28 (m, 4H), 6.92-6.86 (m, 2H), 6.51 (s, 1H), 6.44 (s, 1H), 5.17-5.06 (m, 2H), 4.97-4.88 (m, 2H), 4.58-4.49 (m, 2H), 3.79 (s, 3H), 3.09-2.82 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 179.1, 162.2, 161.0, 159.3, 148.0, 144.6, 140.2, 130.9, 128.8, 127.8, 127.6, 124.8, 122.4, 120.4, 119.8, 118.9, 114.4, 113.9, 93.4, 79.6, 72.4, 58.5, 55.3, 43.9, 29.0; MS (ES+) m/z 451.0 (M+1).

Sources & evidence

ORD record
ord-70d03158418b4af29d2955890761429d
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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