6-Fluoro-1'-(4-methoxybenzyl)-2'-oxo-1',2'-dihydrospiro[1-benzofuran-3,3'-indole]-5-carbonitrile → 6-Fluoro-2'-oxo-1,2'-dihydrospiro[1-benzofuran-3,3'-indole]-5-carbonitrile

HRID 1407633Notes

Reaction equation

HRID 1407633 reaction equation
[F:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]2[C:10]3([CH2:29][O:30][C:4]=2[CH:3]=1)[C:18]1[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=1)[N:12](CC1C=CC(OC)=CC=1)[C:11]3=[O:28].COC1C(C#N)=CC2C3(COC=2C=1)C1C(=CC=CC=1)N(CC1C=CC(OC)=CC=1)C3=O>>[F:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]2[C:10]3([CH2:29][O:30][C:4]=2[CH:3]=1)[C:18]1[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=1)[NH:12][C:11]3=[O:28]

Participants

3

Reactant 2

HCID 593525346-Fluoro-1'-(4-methoxybenzyl)-2'-oxo-1',2'-dihydrospiro[1-benzofuran-3,3'-indole]-5-carbonitrileHCID 593526926-Methoxy-1'-(4-methoxybenzyl)-2'-oxo-1',2'-dihydrospiro[1-benzofuran-3,3'-indole]-5-carbonitrile

Product 1

HCID 593522716-Fluoro-2'-oxo-1,2'-dihydrospiro[1-benzofuran-3,3'-indole]-5-carbonitrile

Procedure

Following the procedure as described in EXAMPLE 3.29 and making non-critical variations using 6-fluoro-1′-(4-methoxybenzyl)-2′-oxo-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-5-carbonitrile to replace of 6-methoxy-1′-(4-methoxybenzyl)-2′-oxo-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-5-carbonitrile, 6-fluoro-2′-oxo-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-5-carbonitrile was obtained (85%): mp 222-224° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.70 (s, 1H), 7.40-7.38 (m, 1H), 7.28-7.23 (m, 2H), 7.17-7.15 (m, 1H), 6.99-6.90 (m, 2H), 4.91 (ABq, 2H); MS (ES+) m/z 280.9 (M+1).

Sources & evidence

ORD record
ord-239ba3c45f57453e93b8228b3e13723c
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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