(3R)-pyrrolidin-3-ol hydrochloride → (R)-1-(3-bromo-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-ol

HRID 1775094Notes

Reaction equation

HRID 1775094 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]2[C:17]3[C:12](=[CH:13][N:14]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:16]=3)[N:11](COCC[Si](C)(C)C)[N:10]=2)=[N:6][C:7]=1F.Cl.[NH:33]1[CH2:37][CH2:36][C@@H:35]([OH:38])[CH2:34]1>>[Br:1][C:2]1[C:7]([N:33]2[CH2:37][CH2:36][C@@H:35]([OH:38])[CH2:34]2)=[N:6][C:5]([C:9]2[C:17]3[C:12](=[CH:13][N:14]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:16]=3)[NH:11][N:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2759336(3R)-pyrrolidin-3-ol hydrochlorideHCID 71253450HCID 71253450, compound

Product 1

HCID 71253352(R)-1-(3-bromo-6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-olYield 9.6%

Procedure

Following the procedures as described in Example 241 and starting with 3-(5-bromo-6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine and (R)-pyrrolidin-3-ol hydrochloride, 293 was obtained as an off-white solid (3.50 mg, 9.60%) over two steps. ESI MS m/z=437.1 (M+1)

Sources & evidence

ORD record
ord-021c702d553643f8bbc3282c61eb3e45
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

Loading…