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

HRID 711254
Notes
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Reaction equation

HRID 711254 reaction equation
Cl.Cl[C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][C:4]=1C.[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[C:18](B(O)O)[CH:17]=[CH:16][N:15]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].CC(O)CC>[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[C:18]([C:3]2[CH:4]=[CH:5][C:6]([CH2:9][NH2:10])=[CH:7][N:8]=2)[CH:17]=[CH:16][N:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 451588802-(Trifluoromethyl)pyridine-4-boronic acidHCID 53395592(6-Chloro-5-methylpyridin-3-yl)methanamine hydrochloride

Product 1

HCID 67208623(2'-(Trifluoromethyl)-2,4'-bipyridin-5-yl)methanamine

Reagents, catalysts & solvents

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

Conditions

Temperature
100 °C

Procedure

To a flask containing (6-chloro-5-methylpyridin-3-yl)methanamine 30-4 (500 mg, 2.20 mmol), 2-(trifluoromethyl)pyridin-4-ylboronic acid 33-1 (418 mg, 2.20 mmol), Pd(OAc)2 (29 mg, 0.11 mmol), S-Phos (91 mg, 0.22 mmol) and potassium phosphate (1.40 g, 6.60 mmol) under Argon was added 2-butanol (4 mL). The mixture was stirred at 100° C. for 10 hours. After cooling to room temperature, the mixture was filtered through celite cake. The filtrate was diluted with ethyl acetate, washed with H2O and brine, dried over Na2SO4, and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, and eluted with 5% methanol containing ˜7N ammonia in dichloromethane to give (2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methanamine 48-1 as a dark yellow solid. MS m/z 268.1 (M+1)

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through celite cake
  3. additionThe filtrate was diluted with ethyl acetate
  4. washwashed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness by rotary evaporation
  7. customThe crude product was purified by silica gel flash chromatography
  8. washeluted with 5% methanol containing ˜7N ammonia in dichloromethane

Sources & evidence

ORD record
ord-5f65d11c70b841fc8e89cd250e4370ec
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181235B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes