3-amino-1'-[2-(trifluoromethyl)benzyl]spiro[furo[3,2-f][1,2]benzisoxazole-5,3'-indol]-2'(1'H)-one → 6-Hydroxy-2'-oxo-1'-[2-(trifluoromethyl)benzyl]-1',2'-dihydrospiro[1-benzofuran-3,3'-indole]-5-carbonitrile
Reaction equation
[NH2:1][C:2]1[C:6]2[CH:7]=[C:8]3[C:13]4([C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[N:15]([CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=5[C:29]([F:32])([F:31])[F:30])[C:14]4=[O:33])[CH2:12][O:11][C:9]3=[CH:10][C:5]=2[O:4]N=1.NC1C2C=C3C4(C5C(=CC=CC=5)N(C[C@H]5CCCO5)C4=O)COC3=CC=2ON=1>>[OH:4][C:5]1[C:6]([C:2]#[N:1])=[CH:7][C:8]2[C:13]3([CH2:12][O:11][C:9]=2[CH:10]=1)[C:21]1[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=1)[N:15]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([F:32])([F:30])[F:31])[C:14]3=[O:33]Participants
Reactant 2
Product 1
Procedure
Following the procedure as described in EXAMPLE 45 and making non-critical variations using 3-amino-1′-[2-(trifluoromethyl)benzyl]spiro[furo[3,2-f][1,2]benzisoxazole-5,3′-indol]-2′(1′H)-one to replace 3-amino-1′-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[furo[3,2-f][1,2]benzisoxazole-5,3′-indol]-2′(1′H)-one, 6-hydroxy-2′-oxo-1′-[2-(trifluoromethyl)benzyl]-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-5-carbonitrile was obtained (38%): mp 122-124° C. (ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 11.30 (s, 1H), 7.81-7.78 (m, 1H), 7.62-7.47 (m, 2H), 7.30-7.23 (m, 3H), 7.18 (s, 1H), 7.08-7.03 (m, 1H), 6.73-6.70 (m, 1H), 6.53 (s, 1H), 5.11-4.83 (m, 4H); 13C NMR (75 MHz, DMSO-d6) δ 178.8, 165.7, 162.1, 141.6, 132.9, 132.7, 131.0, 129.8, 128.1, 127.7, 126.7, 124.7, 124.1, 120.9, 116.7, 110.0, 99.0, 93.2, 81.1, 57.2, 41.0; MS (ES−) m/z 435.1 (M−1).
Sources & evidence
- ORD record
- ord-f079512f751542bfb0d6ae36ea170aae
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263606B2
Reaction notes
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