3-(Trifluoromethyl)phenylboronic acid → 5-(pyridin-3-yl)-3-(3-(trifluoromethyl)phenyl)-1H-pyrazolo[3,4-c]pyridine

HRID 1774969Notes

Reaction equation

HRID 1774969 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10](I)=[N:9][N:8](C3CCCCO3)[C:5]2=[CH:6][N:7]=1.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=1>>[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:2]2[CH:3]=[C:4]3[C:10]([C:24]4[CH:23]=[CH:22][CH:21]=[C:20]([C:19]([F:30])([F:29])[F:18])[CH:25]=4)=[N:9][NH:8][C:5]3=[CH:6][N:7]=2)[CH:32]=1

Participants

4

Reactant 3

HCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 27346563-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 726984825-bromo-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 712538475-(pyridin-3-yl)-3-(3-(trifluoromethyl)phenyl)-1H-pyrazolo[3,4-c]pyridineYield 33%

Procedure

Following the Suzuki coupling procedure of Example 159, 5-bromo-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine and 3-(trifluoromethyl)phenylboronic acid were reacted and the product was consequently reacted under Suzuki coupling procedure of Example 10 with 3-pyridineboronic acid pinacol ester and deprotected by the procedure of Example 131. The mixture was obtained as a base and purified by crystallization from ethyl acetate to afford 56 mg (33%) of 126 over three steps. ESI MS m/z 341.1 (M+1)

Workup

  1. customwere reacted
  2. customThe mixture was obtained as a base
  3. custompurified by crystallization from ethyl acetate

Sources & evidence

ORD record
ord-20ada204a977483ba2c5f17f8d5593c3
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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