4-(4-Chloro-2-fluorobenzyloxy)pyridin-2(1H)-one → HCID 66603475, compound

HRID 1918502Notes

Reaction equation

HRID 1918502 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:16]3[CH:15]4[N:11]([CH2:12][CH2:13][CH2:14]4)[CH2:10][CH2:9][C:8]=3[N:7]([CH3:17])[C:6]=2[N:18]=1.[Cl:19][C:20]1[CH:34]=[CH:33][C:23]([CH2:24][O:25][C:26]2[CH:31]=[CH:30][NH:29][C:28](=[O:32])[CH:27]=2)=[C:22]([F:35])[CH:21]=1>>[ClH:19].[Cl:19][C:20]1[CH:34]=[CH:33][C:23]([CH2:24][O:25][C:26]2[CH:31]=[CH:30][N:29]([C:2]3[CH:3]=[CH:4][C:5]4[C:16]5[CH:15]6[N:11]([CH2:12][CH2:13][CH2:14]6)[CH2:10][CH2:9][C:8]=5[N:7]([CH3:17])[C:6]=4[N:18]=3)[C:28](=[O:32])[CH:27]=2)=[C:22]([F:35])[CH:21]=1

Participants

3

Reactant 2

HCID 580922574-(4-Chloro-2-fluorobenzyloxy)pyridin-2(1H)-oneHCID 58092299HCID 58092299, compound

Product 1

HCID 66603475HCID 66603475, compoundYield 44%

Procedure

9-Bromo-7-methyl-2,3,5,6,7,11c-hexahydro-1H-pyrido[3′,2′:4,5]pyrrolo[2,3-g]indolizine (156 mg, 0.511 mmol) and 4-(4-chloro-2-fluorobenzyloxy)pyridin-2(1H)-one (129 mg, 0.511 mmol) were reacted following the procedure for Example 2 (step b) to provide the title compound (58 mg, 22%) as a yellow solid: mp 150-160° C.; 1H NMR (500 MHz, DMSO-d6) δ 11.30 (s, 1H), 8.11-8.09 (d, J=8.2 Hz, 1H), 7.83-7.81 (d, J=7.7 Hz, 1H), 7.65-7.62 (t, J=8.2 Hz, 1H), 7.55-7.53 (d, J=8.5 Hz, 1H), 7.40-7.36 (m, 2H), 6.17-6.15 (dd, J=7.7, 2.5 Hz, 1H), 6.07-6.05 (d, J=2.5 Hz, 1H), 5.20 (s, 2H), 5.02-5.00 (m, 1H), 3.72 (s, 3H), 3.63-3.34 (m, 3H), 3.32-3.28 (m, 1H), 3.25-3.14 (m, 2H), 2.64-2.55 (m, 1H), 2.14-2.10 (m, 2H), 2.09-1.95 (m, 1H); ESI MS m/z 479 [M+H]+; HPLC (Method B) 95.5% (AUC), tR=14.1 min.

Sources & evidence

ORD record
ord-bfc09d243ae84dd7b55f5b9c763a345f
Source dataset
uspto-grants-2013_12
Patent number
US08618299B2

Reaction notes

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