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Potassium Carbonate → 4-{2-[(3R)-3-methoxypyrrolidin-1-yl]ethyl}-5-methyl-2-[4'-(methylsulfonyl)biphenyl-4-yl]-1,3-oxazole

HRID 1445854
Notes
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Reaction equation

HRID 1445854 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 589514032-(4-Bromophenyl)-4-{2-[(3R)-3-methoxypyrrolidin-1-yl]ethyl}-5-methyl-1,3-oxazole

Product 1

HCID 115466834-{2-[(3R)-3-methoxypyrrolidin-1-yl]ethyl}-5-methyl-2-[4'-(methylsulfonyl)biphenyl-4-yl]-1,3-oxazole
Yield 56.7%

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, 0.014 mmol), anhydrous acetonitrile (4 mL), triphenylphosphine (0.014 g, 0.055 mmol), distilled water (1 mL), 4-(methanesulfonyl)benzeneboronic acid (0.22 g, 1.03 mmol), 2-(4-bromophenyl)-4-{2-[(3R)-3-methoxypyrrolidin-1-yl]ethyl}-5-methyl-1,3-oxazole (See Example 115) (0.25 g, 0.68 mmol) and potassium carbonate (0.28 g, 2.05 mmol) to give the title compound as a white solid (0.17 g): MS (m/e): 441(M+1).

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-13d560b473714218848ad8bc3f94ea11
Source dataset
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07666871B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes