Potassium Carbonate → HCID 68699069, compound

HRID 1445848Notes

Reaction equation

HRID 1445848 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]([CH3:53])=[C:43]([CH2:45][CH2:46][N:47]3[CH2:51][CH2:50][C@H:49]([OH:52])[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>[C:49]([OH:52])(=[O:22])[CH3:50].[OH: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[CH3:53])[CH2:48]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 11660323HCID 11660323, compound

Product 1

HCID 68699069HCID 68699069, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Prepare using the method of Example 103 with palladium (II) acetate (0.002 g, 0.008 mmol), anhydrous acetonitrile (4 mL), triphenylphosphine (0.009 g, 0.034 mmol), distilled water (1 mL), 4-(methanesulfonyl)benzeneboronic acid (0.096 g, 0.45 mmol), (3S)-1-{2-[2-(4-bromophenyl)-5-methyl-1,3-oxazol-4-yl]ethyl}pyrrolidin-3-ol (See Example 108) (0.150 g, 0.43 mmol) and potassium carbonate (0.177 g, 1.28 mmol). Additionally purify using mass guided HPLC to give the title compound as a cream coloured solid (0.035 g): MS (m/e): 427(M+1).

Workup

  1. customPrepare
  2. customAdditionally purify

Sources & evidence

ORD record
ord-b36462cf5f9f4ddeb7693cd6108fc337
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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