Potassium Phosphate, Tribasic → HCID 67208595, compound

HRID 711223Notes

Reaction equation

HRID 711223 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.Cl.[NH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:8][C:4]1[CH:3]=[C:2]([C:15]2[CH:16]=[CH:17][C:12]([CH2:11][NH2:10])=[CH:13][CH:14]=2)[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343114-Aminomethylphenylboronic acid hydrochlorideHCID 27628354-Bromo-2-methylpyridine

Product 1

HCID 67208595HCID 67208595, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
96 °C

Procedure

A mixture of 4-bromo-2-methylpyridine 13-1 (516 mg, 3.00 mmol), (4-(aminomethyl)phenyl)boronic acid hydrochloride 13-2 (422 mg, 2.25 mmol), Pd(PPh3)4 (173 mg, 0.15 mmol) and K3PO4 (1.7 g, 8 mmol) in anhydrous dioxane (10 mL) was stirred at 96° C. under argon overnight. After cooling to room temperature, the mixture was filtered through celite and washed with ethyl acetate. The filtrate was concentrated by rotavap and the residue subjected to silica gel column chromatography with 7% ammonia-saturated methanol in dichloromethane as eluent to give (4-(2-methylpyridin-4-yl)phenyl)methanamine 13-3 as an oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through celite
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated by rotavap

Sources & evidence

ORD record
ord-ba9e72bdce38468ea7672a4724d6345b
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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