3-Fluoroaniline → HCID 59352218, compound

HRID 1965744Notes

Reaction equation

HRID 1965744 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C1(CN)CCCCC1.[O:17]=[C:18]1[C:26]2([CH2:30][O:29][C:28]3[CH:31]=[C:32]4[C:36](=[CH:37][C:27]2=3)[CH2:35][CH2:34][O:33]4)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]1[CH2:38][C:39]1[CH:47]=[CH:46][C:42]([C:43](O)=[O:44])=[CH:41][CH:40]=1.O=C1C2(COC3C=C4C(=CC2=3)CCO4)C2C(=CC=CC=2)N1CC1C=C(C=CC=1)C(O)=O>>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:43](=[O:44])[C:42]2[CH:46]=[CH:47][C:39]([CH2:38][N:19]3[C:20]4[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:26]4([CH2:30][O:29][C:28]5[CH:31]=[C:32]6[C:36](=[CH:37][C:27]4=5)[CH2:35][CH2:34][O:33]6)[C:18]3=[O:17])=[CH:40][CH:41]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 97423-FluoroanilineHCID 76688CyclohexanemethylamineHCID 593522533-[(2'-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-1'(2'H)-yl)methyl]benzoic acidHCID 593526094-[(2'-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-1'(2'H)-yl)methyl]benzoic acid

Product 1

HCID 59352218HCID 59352218, compound

Procedure

Following the procedure as described in EXAMPLE 12 and making non-critical variations using 3-fluoroaniline to replace cyclohexanemethylamine, and 4-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]benzoic acid to replace 3-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]benzoic acid, N-(3-fluorophenyl)-4-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]benzamide was obtained (50%) as a colorless solid: mp>250° C.; 1H NMR (300 MHz, CDCl3) δ8.03 (s, 1H), 7.89-7.82 (m, 2H), 7.63-7.56 (m, 1H), 7.48-7.41 (m, 2H), 7.34-7.15 (m, 4H), 7.09-7.01 (m, 1H), 6.89-6.80 (m, 1H), 6.78-6.72 (m, 1H), 6.47 (s, 1H), 6.42 (s, 1H), 5.01 (ABq, 2H), 4.82 (ABq, 2H), 4.57-4.48 (m, 2H), 3.01-2.92 (m, 2H); 13C NMR (75 MHz, CDCl3) δ178.3, 163.6 (d, JC-F=248.0 Hz), 161.4, 141.7, 139.7, 139.5 (d, JC-F=10.8 Hz), 134.3, 132.4, 130.0 (d, JC-F=9.4 Hz), 128.8, 127.9, 127.6, 124.1, 123.8, 120.0, 119.7, 118.7, 115.4 (d, JC-F=2.9 Hz), 111.2 (d, JC-F=21.3 Hz), 109.2, 107.6 (d, JC-F=26.4 Hz), 93.3, 80.5, 72.4, 57.8, 43.8, 28.9; MS (ES+) m/z 507.2 (M+1).

Sources & evidence

ORD record
ord-8bd265195dae493ba5f5e1badb491f41
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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