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

HRID 1445852Notes

Reaction equation

HRID 1445852 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]([CH2:52][F: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>[F:53][CH2:52][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 116320322-(4-Bromophenyl)-4-{2-[(3R)-3-(fluoromethyl)pyrrolidin-1-yl]ethyl}-5-methyl-1,3-oxazole

Product 1

HCID 116907894-{2-[(3R)-3-(Fluoromethyl)pyrrolidin-1-yl]ethyl}-5-methyl-2-[4'-(methylsulfonyl)biphenyl-4-yl]-1,3-oxazoleYield 36.6%

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, 0.01 mmol), anhydrous acetonitrile (4 mL), triphenylphosphine (0.014 g, 0.05 mmol), distilled water (1 mL), 4-(methanesulfonyl)benzeneboronic acid (0.15 g, 0.71 mmol), 2-(4-bromophenyl)-4-{2-[(3R)-3-(fluoromethyl)pyrrolidin-1-yl]ethyl}-5-methyl-1,3-oxazole (See Example 112) (0.25 g, 0.68 mmol) and potassium carbonate (0.28 g, 2.04 mmol). Additionally triturate the resulting solid with 2:1 diethyl ether:ethyl acetate to give the title compound as a pale yellow coloured solid (0.11 g): MS (m/e): 443 (M+1).

Workup

  1. customPrepare
  2. customAdditionally triturate the resulting solid with 2:1 diethyl ether

Sources & evidence

ORD record
ord-c72353d9d1d54f83b772567f6aeebb24
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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