4-(4-Chloro-2-fluorobenzyloxy)pyridin-2(1H)-one → HCID 66603505, compound

HRID 1918503Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH2:10][N:11]4[CH:15]([CH2:16][C:8]=3[N:7]([CH3:17])[C:6]=2[N:18]=1)[CH2:14][CH2:13][CH2:12]4.[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:9]5[CH2:10][N:11]6[CH:15]([CH2:16][C:8]=5[N:7]([CH3:17])[C:6]=4[N:18]=3)[CH2:14][CH2:13][CH2:12]6)[C:28](=[O:32])[CH:27]=2)=[C:22]([F:35])[CH:21]=1

Participants

Reactant 2

HCID 580922574-(4-Chloro-2-fluorobenzyloxy)pyridin-2(1H)-one

HCID 58092313HCID 58092313, compound

Product 1

HCID 66603505HCID 66603505, compoundYield 53.7%

Procedure

2-Bromo-11-methyl-5,7,8,9,9a,10-hexahydro-11H-pyrido[3′,2′:4,5]pyrrolo[3,2-f]indolizine (150 mg, 0.491 mmol) and 4-(4-chloro-2-fluorobenzyloxy)pyridin-2(1H)-one (124 mg, 0.491 mmol) were reacted following the procedure for Example 2 (step b) to provide the title compound (68 mg, 27%) as a yellow solid: mp 210-220° C.; 1H NMR (500 MHz, DMSO-d6) δ 10.95 (s, 1H), 8.06 (d, J=8.3 Hz, 1H), 7.84-7.82 (d, J=7.8 Hz, 1H), 7.65-7.62 (t, J=Hz, 1H), 7.56-7.53 (dd, J=9.9, 2.0 Hz, 1H), 7.39-7.37 (m, 2H), 6.17-6.16 (dd, J=7.8, 2.7 Hz, 1H), 6.06 (d, J=2.7 Hz, 1H), 5.20 (s, 2H), 4.82-4.78 (dd, J=14.0, 2.4 Hz, 1H), 4.35-4.30 (m, 1H), 3.91-3.71 (m, 5H), 3.50 (m, 1H), 3.30-3.26 (m, 1H), 3.12-3.06 (m, 1H), 2.47-2.42 (m, 1H), 2.19-2.07 (m, 2H), 1.93-1.86 (m, 1H); ESI MS m/z 479 [M+H]+; HPLC (Method B) 98.1% (AUC), tR=13.9 min.

Sources & evidence

ORD record: ord-755233b474534456b347ef5aeb419c0d
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618299B2

Reaction notes

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