Water → HCID 86627636, compound

HRID 604682Notes

Reaction equation

HRID 604682 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25](Br)=[CH:24][CH:23]=[C:22]([Cl:27])[N:21]=3)[C@H:14]2[CH3:28])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[Cl:31][C:32]1[CH:33]=[CH:34][C:35]([O:41][CH3:42])=[C:36](B(O)O)[CH:37]=1.C([O-])([O-])=O.[K+].[K+].O>C1COCC1.[Pd](Cl)Cl.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2]>[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:34]4[CH:33]=[C:32]([Cl:31])[CH:37]=[CH:36][C:35]=4[O:41][CH3:42])=[CH:24][CH:23]=[C:22]([Cl:27])[N:21]=3)[C@H:14]2[CH3:28])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27357515-Chloro-2-methoxyphenylboronic acidHCID 57576268(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[(3-bromo-6-chloropyridin-2-yl)methyl]-4-methyl-1,3-oxazolidin-2-one

Product 1

HCID 86627636HCID 86627636, compound

Reagents, catalysts & solvents 2

HCID 178454861HCID 178454861, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1,1′-bis(di-t-butylphosphino)ferrocene palladium dichloride (0.263 g, 0.386 mmol) was added to a stirred, degassed mixture of INTERMEDIATE 9 (4.00 g, 7.73 mmol), 5-chloro-2-methoxy phenyl boronic acid (1.44 g, 7.73 mmol) and K2CO3 (4.27 g, 30.9 mmol) in THF (30 mL). The mixture was stirred at room temperature for 1 h. LCMS showed that no starting material was left. Water was added and the mixture was extracted with EtOAc (3×60 mL). The combined organic layers were washed with brine and dried (Na2SO4). The title compound was obtained as a colorless solid after flash chromatography using CH2Cl2/hexane (8:2) as the eluant.

Workup

  1. customdegassed
  2. waitwas left
  3. extractionthe mixture was extracted with EtOAc (3×60 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-58043ea6a8c44f7aa1b9a1fa17f99f96
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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