6-fluoro-2'-oxo-1'-[[3-(trifluoromethyl)pyridin-2-yl]methyl]spiro[2H-1-benzofuran-3,3'-indole]-5-carbonitrile → 1'-((3-(Trifluoromethyl)pyridin-2-yl)methyl)-1,6-dihydrospiro[furo[3,2-f]indazole-5,3'-indolin]-2'-one

HRID 2385576Notes

Reaction equation

HRID 2385576 reaction equation
F[C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]2[C:10]3([CH2:31][O:32][C:4]=2[CH:3]=1)[C:18]1[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=1)[N:12]([CH2:19][C:20]1[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][N:21]=1)[C:11]3=[O:30].FC1C(C#[N:41])=CC2C3(COC=2C=1)C1C(=CC=CC=1)N(CC1C=CC=CC=1C(F)(F)F)C3=O>>[F:29][C:26]([F:28])([F:27])[C:25]1[C:20]([CH2:19][N:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]3([C:5]4[CH:6]=[C:7]5[C:2](=[CH:3][C:4]=4[O:32][CH2:31]3)[NH:41][N:9]=[CH:8]5)[C:11]2=[O:30])=[N:21][CH:22]=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 593521886-fluoro-2'-oxo-1'-[[3-(trifluoromethyl)pyridin-2-yl]methyl]spiro[2H-1-benzofuran-3,3'-indole]-5-carbonitrileHCID 593526726-Fluoro-2'-oxo-1'-[2-(trifluoromethyl)benzyl]-1',2'-dihydrospiro[1-benzofuran-3,3-indole]-5-carbonitrile

Product 1

HCID 461959881'-((3-(Trifluoromethyl)pyridin-2-yl)methyl)-1,6-dihydrospiro[furo[3,2-f]indazole-5,3'-indolin]-2'-one

Procedure

Following the procedure as described in EXAMPLE 46 and making non-critical variations using 6-fluoro-2′-oxo-1′-{[3-(trifluoromethyl)pyridin-2-yl]methyl}-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-5-carbonitrile to replace 6-fluoro-2′-oxo-1′-[2-(trifluoromethyl)benzyl]-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-5-carbonitrile, 1′-((3-(trifluoromethyl)pyridin-2-yl)methyl)-1,6-dihydrospiro[furo[3,2-f]indazole-5,3′-indolin]-2′-one was obtained (47%): mp 152-154° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 12.79 (br s, 1H), 8.80 (d, J=6.0 Hz, 1H), 8.24-8.21 (m, 1H), 7.87 (s, 1H), 7.57-7.53 (m, 1H), 7.26-7.17 (m, 3H), 7.02-6.89 (m, 3H), 5.25 (ABq, 2H), 4.87 (ABq, 2H); 13C NMR (75 MHz, DMSO-d6) δ 172.5, 160.1, 153.2, 152.9, 143.5, 141.6, 135.5, 135.4, 134.1, 132.7, 129.1, 126.7, 124.0, 123.6, 123.2, 122.5, 119.1, 116.0, 109.5, 89.4, 80.0, 56.9, 42.4; MS (ES+) m/z 436.9 (M+1).

Sources & evidence

ORD record
ord-9ed4fa7f19f144788ff7dbd3c5239f66
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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