Potassium Carbonate → HCID 11682338, compound

HRID 1445860Notes

Reaction equation

HRID 1445860 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][O:21][C:22]1[N:27]=[CH:26][C:25](B(O)O)=[CH:24][N:23]=1.Br[C:32]1[CH:37]=[CH:36][C:35]([C:38]2[O:39][C:40]([CH3:51])=[C:41]([CH2:43][CH2:44][N:45]3[CH2:49][CH2:48][CH2:47][C@H:46]3[CH3:50])[N:42]=2)=[CH:34][CH:33]=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(#N)C>[CH3:20][O:21][C:22]1[N:27]=[CH:26][C:25]([C:32]2[CH:37]=[CH:36][C:35]([C:38]3[O:39][C:40]([CH3:51])=[C:41]([CH2:43][CH2:44][N:45]4[CH2:49][CH2:48][CH2:47][C@H:46]4[CH3:50])[N:42]=3)=[CH:34][CH:33]=2)=[CH:24][N:23]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27367782-Methoxypyrimidine-5-boronic acidHCID 11530378HCID 11530378, compound2×

Product 1

HCID 11682338HCID 11682338, compoundYield 1.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Prepare using the method of Example 103 with palladium (II) acetate (0.011 g, 0.05 mmol), anhydrous acetonitrile (8 mL), triphenylphosphine (0.051 g, 0.19 mmol), distilled water (2 mL), 2-methoxy-5-pyrimidineboronic acid (0.75 g, 4.87 mmol), 2-(4-bromophenyl)-4-{2-[(2R)-2-methylpyrrolidin-1-yl]ethyl}-5-methyl-1,3-oxazole (See Intermediate 73) (0.85 g, 2.43 mmol) and potassium carbonate (0.1.01 g, 7.30 mmol). Additionally recrystallise from acetonitrile/ethyl acetate to give the title compound as a cream coloured solid (0.016 g): MS (m/e): 379(M+1).

Workup

  1. customPrepare
  2. customAdditionally recrystallise from acetonitrile/ethyl acetate

Sources & evidence

ORD record
ord-bf5e64934318448bb86d5ff5033287e9
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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