5-Bromo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazole → 4-((5-Chloropyridin-2-yl)methoxy)-1-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one hydrochloride

HRID 2387515Notes

Reaction equation

HRID 2387515 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[N:6]=[CH:5]2.[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][O:26][C:27]2[CH:32]=[CH:31][NH:30][C:29](=[O:33])[CH:28]=2)=[N:23][CH:24]=1>>[ClH:18].[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][O:26][C:27]2[CH:32]=[CH:31][N:30]([C:2]3[CH:3]=[C:4]4[C:8](=[CH:9][CH:10]=3)[N:7]([CH2:11][CH2:12][N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[N:6]=[CH:5]4)[C:29](=[O:33])[CH:28]=2)=[N:23][CH:24]=1

Participants

3

Reactant 2

HCID 576255415-Bromo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazoleHCID 579503474-((5-chloropyridin-2-yl)methoxy)pyridin-2(1H)-one

Product 1

HCID 684595494-((5-Chloropyridin-2-yl)methoxy)-1-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one hydrochlorideYield 72%

Procedure

5-Bromo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazole (200 mg, 0.68 mmol) and 4-((5-chloropyridin-2-yl)methoxy)pyridin-2(1H)-one (160 mg, 0.68 mmol) were reacted according to the procedure in Example 63 (step c) to provide the title compound (119 mg, 36%) as a brown solid: mp 95-101° C. deliquesced; 1H NMR (500 MHz, CD3OD) δ 8.63 (s, 1H), 8.23 (s, 1H), 8.00-7.98 (dd, J=8.3, 2.1 Hz, 1H), 7.82 (d, J=19 Hz, 1H), 7.79 (d, J=8.9 Hz, 1H), 7.66-7.64 (2 overlapping d, J=8.5, 7.6 Hz, 2H), 7.47-7.44 (dd, J=8.9, 1.8 Hz, 1H), 6.41-6.39 (dd, J=7.5, 2.8 Hz, 1H), 6.16 (d, J=2.6 Hz, 1H), 5.30 (s, 2H), 4.87 (t, J=5.9 Hz, 2H), 3.86 (t, J=5.9 Hz, 2H), 3.72 (m, 2H), 3.19-3.13 (m, 2H), 2.18-2.15 (m, 2H), 2.03-1.99 (m, 2H); ESI MS m/z 450 [M+H]+; HPLC (Method D) 97.4% (AUC), tR=11.9 min.

Sources & evidence

ORD record
ord-7ad6d38162b44536b3127e8255af4e1f
Source dataset
uspto-grants-2012_09
Patent number
US08268868B2

Reaction notes

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