Cesium carbonate → 2-(6-Bromopyridin-3-yl)pyrimidine

HRID 1038006

Reaction equation

HRID 1038006 reaction equation
Br[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][N:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CO.C1(C)C=CC=CC=1.O.CCOC(C)=O.O.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>[Br:8][C:9]1[N:10]=[CH:11][C:12]([C:2]2[N:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:13][CH:14]=1

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 783452-BromopyrimidineHCID 27627062-Bromopyridine-5-boronic acid

Product 1

HCID 534869812-(6-Bromopyridin-3-yl)pyrimidine

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 70394911HCID 70394911, compoundSolvent

Procedure

A mixture of 2-bromopyrimidine (0.43 g, 2.70 mmol), 2-bromopyridine-5-boronic acid (0.55 g, 2.72 mmol), tetrakis(triphenylphosphine)palladium(0) (300 mg, 0.259 mmol), cesium carbonate (1.15 g, 3.03 mmol) was stirred in MeOH/toluene/water (15 ml, 1/1/1) at reflux temperature overnight. The reaction was cooled to room temperature and diluted with EtOAc (200 ml) and water (50 ml). The organic layer was separated, dried over MgSO4, filtered and solvent evaporated yielding a residue which was purified on silica gel eluting with 25% v/v EtOAc/hexanes yielding product 76 as white solid. (0.55 g, 85%) ESMS (MH, 236).

Workup

  1. temperatureat reflux temperature overnight
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customsolvent evaporated
  6. customyielding a residue which
  7. customwas purified on silica gel eluting with 25% v/v EtOAc/hexanes yielding product 76 as white solid

Sources & evidence

ORD record
ord-3b030c67ac524dd68b2377a2e3658020
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Linked notes

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