4-(Methanesulfonyl)phenylboronic acid → 2-[2-(3-Fluoro-4'-methanesulfonyl-biphenyl-4-yl)-5-methyl-oxazol-4-yl]-ethanol

HRID 1445764Notes

Reaction equation

HRID 1445764 reaction equation
C([O:8][CH2:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20](Br)=[CH:19][C:18]=2[F:24])[O:14][C:15]=1[CH3:16])C1C=CC=CC=1.[CH3:25][S:26]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)(=[O:28])=[O:27]>O1CCCC1.[OH-].[OH-].[Pd+2]>[F:24][C:18]1[CH:19]=[C:20]([C:32]2[CH:33]=[CH:34][C:29]([S:26]([CH3:25])(=[O:28])=[O:27])=[CH:30][CH:31]=2)[CH:21]=[CH:22][C:17]=1[C:13]1[O:14][C:15]([CH3:16])=[C:11]([CH2:10][CH2:9][OH:8])[N:12]=1

Participants

5

Reactant 2

HCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 589514114-(2-Benzyloxy-ethyl)-2-(4-bromo-2-fluoro-phenyl)-5-methyl-oxazole2×

Product 1

HCID 589514052-[2-(3-Fluoro-4'-methanesulfonyl-biphenyl-4-yl)-5-methyl-oxazol-4-yl]-ethanol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Using 4-(2-benzyloxy-ethyl)-2-(4-bromo-2-fluoro-phenyl)-5-methyl-oxazole (see Intermediate 37) and 4-methylsulfonylphenylboronic acid, follow a procedure in substantial accordance with that found in Example 4. Take this product and hydrogenate using 20% palladium hydroxide on carbon in tetrahydrofuran for 36 hours at 40° C. and 60 psi. After this time, filter the reaction and concentrate in vacuo. Purify via radial chromatography eluting with methanol and dichloromethane. MS (m/e): 376.2 (M+1)

Workup

  1. customfor 36 hours
  2. customat 40° C.
  3. filtrationAfter this time, filter
  4. customthe reaction
  5. concentrationconcentrate in vacuo
  6. customPurify via radial chromatography
  7. washeluting with methanol and dichloromethane

Sources & evidence

ORD record
ord-26e14d612a1549ca9e9edf27ed6c8483
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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