Potassium Phosphate, Tribasic → (2'-Fluoro-2,4'-bipyridin-5-yl)methanamine

HRID 711234Notes

Reaction equation

HRID 711234 reaction equation
[F:1][C:2]1[CH:7]=[C:6](B(O)O)[CH:5]=[CH:4][N:3]=1.Cl[C:12]1[N:17]=[CH:16][C:15]([CH2:18][NH2:19])=[CH:14][CH:13]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CC(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:1][C:2]1[CH:7]=[C:6]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][NH2:19])=[CH:16][N:17]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27833962-Fluoropyridine-4-boronic acidHCID 70209275-(Aminomethyl)-2-chloropyridineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 67208618(2'-Fluoro-2,4'-bipyridin-5-yl)methanamine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6568(+-)-2-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (2-fluoropyridin-4-yl)boronic acid 24-1 (200 mg, 1.42 mmol), (6-chloropyridin-3-yl)methanamine 18-1 (142 mg, 1.00 mmol), Pd(OAc)2 (12 mg, 0.05 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (41 mg, 0.1 mmol) and K3PO4 (424 mg, 2.00 mmol) in 2-butanol (1 mL) was stirred at 100° C. under argon overnight. After cooling to room temperature, the mixture was filtered through celite (washed with ethyl acetate), concentrated by rotavap and the residue subjected to silica gel column chromatography with 7% ammonia-saturated methanol in dichloromethane as eluent to give (2′-fluoro-[2,4′-bipyridin]-5-yl)methanamine 24-2 as an oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through celite (washed with ethyl acetate)
  3. concentrationconcentrated by rotavap

Sources & evidence

ORD record
ord-cca6523a3e654ac1ad30858122f65748
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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