Potassium Carbonate → HCID 11717798, compound

HRID 1445859Notes

Reaction equation

HRID 1445859 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([C:22]1[S:26][C:25](B(O)O)=[CH:24][CH:23]=1)#[N:21].Br[C:31]1[CH:36]=[CH:35][C:34]([C:37]2[O:38][C:39]([CH3:50])=[C:40]([CH2:42][CH2:43][N:44]3[CH2:48][CH2:47][CH2:46][C@H:45]3[CH3:49])[N:41]=2)=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)C.O.C1(C)C=CC=CC=1>[CH3:50][C:39]1[O:38][C:37]([C:34]2[CH:35]=[CH:36][C:31]([C:25]3[S:26][C:22]([C:20]#[N:21])=[CH:23][CH:24]=3)=[CH:32][CH:33]=2)=[N:41][C:40]=1[CH2:42][CH2:43][N:44]1[CH2:48][CH2:47][CH2:46][C@H:45]1[CH3:49]

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 41987435-Cyanothiophene-2-boronic acidHCID 11530378HCID 11530378, compound2×

Product 1

HCID 11717798HCID 11717798, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Prepare using the method of Example 120 with palladium (II) acetate (0.008 g, 0.04 mmol), anhydrous toluene (5 mL), triphenylphosphine (0.038 g, 0.15 mmol), distilled water (1.5 mL), ethanol (1 mL), 5-cyanothiophene-2-boronic acid (0.21 g, 1.37 mmol), 2-(4-bromophenyl)-4-{2-[(2R)-2-methylpyrrolidin-1-yl]ethyl}-5-methyl-1,3-oxazole (See Intermediate 73) (0.32 g, 0.92 mmol) and potassium carbonate (0.38 g, 2.75 mmol). Additionally purify by trituration with ethyl acetate to give the title compound as a cream coloured solid (0.03 g): MS (m/e): 378(M+1).

Workup

  1. customPrepare
  2. customAdditionally purify by trituration with ethyl acetate

Sources & evidence

ORD record
ord-a7849ac74e8b44c587618f6981470fec
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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