1-(diphenylmethyl)-3-(2-hydroxy-4-methoxy-5-methylphenyl)-1,3-dihydro-2H-indol-2-one → 6-((5-(trifluoromethyl)furan-2-yl)methyl)-2,3,5',6'-tetrahydro-2'H-spiro[[1,4]dioxino[2,3-f]indole-8,3'-benzofuro[6,5-b]furan]-7(6H)-one

HRID 1407582Notes

Reaction equation

HRID 1407582 reaction equation
[OH:1][C:2]1[C:10]([CH:11]2[C:19]3[CH:18]=[C:17]4[O:20][CH2:21][CH2:22][O:23][C:16]4=[CH:15][C:14]=3[N:13]([CH2:24][C:25]3[O:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=3)[C:12]2=[O:34])=[CH:9][C:5]2[CH2:6][CH2:7][O:8][C:4]=2[CH:3]=1.[C:35]1(C(C2C=CC=CC=2)N2C3C(=CC=CC=3)C(C3C=C(C)C(OC)=CC=3O)C2=O)C=CC=CC=1>>[F:31][C:30]([F:33])([F:32])[C:27]1[O:26][C:25]([CH2:24][N:13]2[C:14]3[CH:15]=[C:16]4[O:23][CH2:22][CH2:21][O:20][C:17]4=[CH:18][C:19]=3[C:11]3([C:10]4=[CH:9][C:5]5[CH2:6][CH2:7][O:8][C:4]=5[CH:3]=[C:2]4[O:1][CH2:35]3)[C:12]2=[O:34])=[CH:29][CH:28]=1

Participants

3

Reactant 2

HCID 673563761-(diphenylmethyl)-3-(2-hydroxy-4-methoxy-5-methylphenyl)-1,3-dihydro-2H-indol-2-oneHCID 685980268-(6-hydroxy-2,3-dihydrobenzofuran-5-yl)-6-((5-(trifluoromethyl)furan-2-yl)methyl)-6,8-dihydro-2H-[1,4]dioxino[2,3-f]indol-7(3H)-one

Product 1

HCID 593522726-((5-(trifluoromethyl)furan-2-yl)methyl)-2,3,5',6'-tetrahydro-2'H-spiro[[1,4]dioxino[2,3-f]indole-8,3'-benzofuro[6,5-b]furan]-7(6H)-one

Procedure

Following the procedure as described in EXAMPLE 2 and making non-critical variations using 8-(6-hydroxy-2,3-dihydrobenzofuran-5-yl)-6-((5-(trifluoromethyl)furan-2-yl)methyl)-6,8-dihydro-2H-[1,4]dioxino[2,3-f]indol-7(3H)-one to replace 1-(diphenylmethyl)-3-(2-hydroxy-4-methoxy-5-methylphenyl)-1,3-dihydro-2H-indol-2-one, 6-((5-(trifluoromethyl)furan-2-yl)methyl)-2,3,5′,6′-tetrahydro-2′H-spiro[[1,4]dioxino[2,3-f]indole-8,3′-benzofuro[6,5-b]furan]-7(6H)-one was obtained (42%) as a colorless solid: mp 189-191° C.; 1H NMR (300 MHz, CDCl3) δ6.77-6.73 (m, 1H), 6.72 (s, 1H), 6.52-6.45 (m, 2H), 6.43-6.36 (m, 2H), 4.91 (ABq, 2H), 4.77 (ABq, 2H), 4.53 (t, J=8.6 Hz, 2H), 4.27-4.14 (m, 4H), 3.10-2.90 (m, 2H); 13C NMR (75 MHz, CDCl3) δ177.6, 161.8, 161.0, 151.9, 143.9, 140.1, 135.2, 124.9, 120.2, 120.0, 118.8, 113.6, 112.6 (d, J=2.8 Hz, 1C), 109.2, 98.8, 93.1, 80.4, 72.4, 64.6, 64.0, 57.5, 37.0, 28.9; MS (ES+) m/z 485.9 (M+1).

Sources & evidence

ORD record
ord-ffbb3de7b1cd47ce8c193be944f5cafc
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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