Ethanol → HCID 58207951, compound

HRID 2197560Notes

Reaction equation

HRID 2197560 reaction equation
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[F:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(O)C>C1(C)C=CC=CC=1.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.C(OCC)(=O)C>[Br:8][C:6]1[CH:7]=[C:2]([C:14]2[CH:13]=[CH:12][C:11]([F:10])=[CH:16][C:15]=2[F:17])[C:3]([NH2:9])=[N:4][CH:5]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 62657Potassium Phosphate, TribasicHCID 988513,5-Dibromo-2-pyridylamineHCID 27343342,4-Difluorophenylboronic acid

Product 1

HCID 58207951HCID 58207951, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3,5-dibromopyridin-2-amine (2.95 g, 11.71 mmol) and 2,4-difluorophenylboronic acid (1.85 g, 11.71 mmol) in toluene was degassed via nitrogen bubble for 20 mins. The mixture was then added Pd(PPh3)4 (0.677 g, 0.585 mmol), K3PO4 (2 M, 11.8 mL, 23.4 mmol) and ethanol (1 mL) and heated at 80° C. overnight. The reaction was cooled, poured into ethyl acetate (150 mL), washed with brine, separated, dried over Na2SO4 and concentrated to give a crude 5-bromo-3-(2,4-difluorophenyl)pyridin-2-amine (3) which was used directly in next step without purification.

Workup

  1. custombubble for 20 mins
  2. temperatureThe reaction was cooled
  3. washwashed with brine
  4. customseparated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cf2e1b3c390a4719aad22fa368700c76
Source dataset
uspto-grants-2012_12
Patent number
US08338604B2

Reaction notes

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