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Cesium fluoride → 2',3'-difluoro-5-{(1R)-1-[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]ethoxy}-3,4'-bipyridin-6-amine

HRID 1406323
Notes
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Reaction equation

HRID 1406323 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:9][C@@H:10]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[N:19]2[N:23]=[CH:22][CH:21]=[N:20]2)[CH3:11])[C:5]([NH2:8])=[N:6][CH:7]=1.[F:24][C:25]1[C:30]([F:31])=[C:29](B(O)O)[CH:28]=[CH:27][N:26]=1.[F-].[Cs+]>CO.O>[F:24][C:25]1[C:30]([F:31])=[C:29]([C:2]2[CH:7]=[N:6][C:5]([NH2:8])=[C:4]([O:9][C@@H:10]([C:12]3[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=3[N:19]3[N:23]=[CH:22][CH:21]=[N:20]3)[CH3:11])[CH:3]=2)[CH:28]=[CH:27][N:26]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 49761750(2,3-Difluoropyridin-4-yl)boronic acidHCID 67468125(R)-5-bromo-3-(1-(5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl)ethoxy)pyridin-2-amine

Product 1

HCID 674669252',3'-difluoro-5-{(1R)-1-[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]ethoxy}-3,4'-bipyridin-6-amineYield 79.8%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

5-Bromo-3-[(R)-1-(5-fluoro-2-[1,2,3]triazol-2-yl-phenyl)-ethoxy]-pyridin-2-ylamine (example 45) (200 mg, 0.529 mmol, 1.0 eq) and 2,3-difluoropyridin-4-ylboronic acid (168 mg, 1.06 mmol, 2.0 eq) were dissolved in MeOH (5 mL), followed by the addition of freshly prepared aqueous solution of CsF (563 mg, 3.5 mmol, 7 eq) in water (3.34 mL) and Pd-132 (64 mg, 0.09 mmol, 0.17 eq), then degassed for three times. The mixture was heated up to 80° C. for overnight. LCMS showed >80% conversion to desired product, and ˜10% of des-bromation of example 45. The reaction mixture was filtered. The filtrate was concentrated and purified via a Biotage silica gel cartridge to provide the title compound (174 mg) as a white solid.

Workup

  1. customdegassed for three times
  2. filtrationThe reaction mixture was filtered
  3. concentrationThe filtrate was concentrated
  4. custompurified via a Biotage silica gel cartridge

Sources & evidence

ORD record
ord-d1399d1954f24782aa29822e2cb7cc83
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08916593B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes