Potassium Phosphate, Tribasic → (2',3-Dimethyl-[2,4'-bipyridin]-5-yl)methanamine

HRID 711268Notes

Reaction equation

HRID 711268 reaction equation
Cl.Cl[C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][C:4]=1[CH3:11].FC1C=C(CN)C=CC=1[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([CH3:25])[CH:20]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:25][C:21]1[CH:20]=[C:19]([C:3]2[C:4]([CH3:11])=[CH:5][C:6]([CH2:9][NH2:10])=[CH:7][N:8]=2)[CH:24]=[CH:23][N:22]=1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 53395592(6-Chloro-5-methylpyridin-3-yl)methanamine hydrochlorideHCID 67208674(3-Fluoro-4-(2-methylpyridin-4-yl)phenyl)methanamine

Product 1

HCID 66632694(2',3-Dimethyl-[2,4'-bipyridin]-5-yl)methanamine

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

To a reaction vial was added (6-chloro-5-methylpyridin-3-yl)methanamine 30-4 (500 mg, 2.6 mmol), 2-methylpyridin-4-ylboronic acid 15-1 (460 mg, 3.38 mmol), Pd(OAc)2 (58 mg, 0.26 mmol), S-Phos (150 mg, 0.37 mmol) and K3PO4 (1.65 g, 7.8 mmol). The vial was evacuated and backfilled with nitrogen. 2-butanol (5 mL) was added via syringe. The reaction was stirred at room temperature for 10 mins and then 110° C. for 2 hours. After cooling to room temperature, the reaction mixture was diluted into 10% methanol in DCM, and filtered through celite pad. The filtrate was dried and the crude product was purified by silica gel flash chromatography, and eluted with 10% methanol in DCM to give (2′,3-dimethyl-2,4′-bipyridin-5-yl)methanamine 63-2 as an oil. MS m/z 214.2 (M+1).

Workup

  1. customThe vial was evacuated
  2. addition2-butanol (5 mL) was added via syringe
  3. wait110° C. for 2 hours
  4. temperatureAfter cooling to room temperature
  5. additionthe reaction mixture was diluted into 10% methanol in DCM
  6. filtrationfiltered through celite pad
  7. customThe filtrate was dried
  8. customthe crude product was purified by silica gel flash chromatography
  9. washeluted with 10% methanol in DCM

Sources & evidence

ORD record
ord-0d5df8221f8d4a9c8f0182117ba82550
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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