Potassium Carbonate → HCID 11676556, compound

HRID 1445856Notes

Reaction equation

HRID 1445856 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][S:21]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)(=[O:23])=[O:22].Br[C:34]1[CH:39]=[CH:38][C:37]([C:40]2[O:41][C:42]([CH3:54])=[C:43]([CH2:45][CH2:46][N:47]3[CH2:51][CH2:50][C@H:49]([O:52][CH3:53])[CH2:48]3)[N:44]=2)=[CH:36][CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(#N)C>[CH3:53][O:52][C@H:49]1[CH2:50][CH2:51][N:47]([CH2:46][CH2:45][C:43]2[N:44]=[C:40]([C:37]3[CH:38]=[CH:39][C:34]([C:27]4[CH:28]=[CH:29][C:24]([S:21]([CH3:20])(=[O:23])=[O:22])=[CH:25][CH:26]=4)=[CH:35][CH:36]=3)[O:41][C:42]=2[CH3:54])[CH2:48]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 11603028HCID 11603028, compound

Product 1

HCID 11676556HCID 11676556, compoundYield 36.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Prepare using the method of Example 103 with palladium (II) acetate (0.003 g, 0.015 mmol), anhydrous acetonitrile (4 mL), triphenylphosphine (0.016 g, 0.059 mmol), distilled water (1 mL), 4-(methanesulfonyl)benzeneboronic acid (0.24 g, 1.11 mmol), 2-(4-bromophenyl)-4-{2-[(3S)-3-methoxypyrrolidin-1-yl]ethyl}-5-methyl-1,3-oxazole (See Example 117) (0.27 g, 0.74 mmol) and potassium carbonate (0.31 g, 2.22 mmol) to give the title compound as a white solid (0.12 g): MS (m/e): 441(M+1).

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-9cdf0e00eafe4bf2bf204326cc82496b
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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