1'-(diphenylmethyl)-6-methoxy-5-methylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one → 5-fluoro-6-methoxyspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 1407617Notes

Reaction equation

HRID 1407617 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3([C:20]4[CH:21]=[C:22]([F:27])[C:23]([O:25][CH3:26])=[CH:24][C:19]=4[O:18][CH2:17]3)[C:9]2=[O:28])C=CC=CC=1.C1(C(C2C=CC=CC=2)N2C3C(=CC=CC=3)C3(C4C=C(C)C(OC)=CC=4OC3)C2=O)C=CC=CC=1>>[F:27][C:22]1[C:23]([O:25][CH3:26])=[CH:24][C:19]2[O:18][CH2:17][C:10]3([C:11]4[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=4)[NH:8][C:9]3=[O:28])[C:20]=2[CH:21]=1

Participants

3

Reactant 2

HCID 593524081'-(diphenylmethyl)-6-methoxy-5-methylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneHCID 593526021'-(diphenylmethyl)-5-fluoro-6-methoxyspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

Product 1

HCID 461940485-fluoro-6-methoxyspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

Procedure

Following the procedure as described in EXAMPLE 3 and making non-critical variations using 1′-(diphenylmethyl)-5-fluoro-6-methoxyspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one to replace 1′-(diphenylmethyl)-6-methoxy-5-methylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one, 5-fluoro-6-methoxyspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one was obtained (82%) as a colorless solid: mp 222-225° C.; 1H NMR (300 MHz, CDCl3) δ8.33 (s, 1H), 7.29-7.21 (m, 1H), 7.12 (d, J=6.7 Hz, 1H), 7.03 (ddd, J=7.5, 7.5, 0.9 Hz, 1H), 6.93 (d, J=7.8 Hz, 1H), 6.59 (d, J=6.8 Hz, 1H), 6.52 (d, J=10.1 Hz, 1H), 4.96 (d, J=9.1 Hz, 1H), 4.68 (d, J=9.1 Hz, 1H), 3.85 (s, 3H); 13C NMR (75 MHz, CDCl3) δ179.9, 157.2, 149.3, 149.1 (d, J=12.4 Hz), 146.1, 140.2, 132.2, 129.1, 123.8 (d, J=42.8 Hz), 118.6 (d, J=7.1 Hz), 110.7, 110.4, 96.3, 80.5, 58.6, 56.4; MS (ES+) m/z 286.2 (M+1).

Sources & evidence

ORD record
ord-aee1c9f6ecbb496e80a42382f7f2e988
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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