Sodium Carbonate → (4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-{[6-chloro-3-(2-fluoro-5-nitrophenyl)pyridin-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

HRID 604681Notes

Reaction equation

HRID 604681 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.[F:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][C:33]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>O.CCO.C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[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:33]4[CH:34]=[C:35]([N+:38]([O-:40])=[O:39])[CH:36]=[CH:37][C:32]=4[F:31])=[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

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2763280(2-Fluoro-5-nitrophenyl)boronic 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 86627635(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-{[6-chloro-3-(2-fluoro-5-nitrophenyl)pyridin-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

A mixture of INTERMEDIATE 9 (1.0 g, 1.93 mmol), 2-fluoro-5-nitro phenyl boronic acid (0.51 g, 2.74 mmol), tetrakis(triphenylphosphine) palladium (223 mg, 10% mol) and Na2CO3 (410 mg, 3.86 mmol) in 14 mL of water/EtOH/toluene (1:2:4) was heated at reflux for 2 h. The solvents were removed. Water (20 mL) was added. The organic was extracted with CH2Cl2 (3×10 mL). The combined CH2Cl2 layers were washed with brine, and dried (Na2SO4). The title compound was obtained after flash chromatography using CH2Cl2/hexane (8:2) as the eluant. LCMS M+H 578.30.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. customThe solvents were removed
  4. additionWater (20 mL) was added
  5. extractionThe organic was extracted with CH2Cl2 (3×10 mL)
  6. washThe combined CH2Cl2 layers were washed with brine
  7. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-7fa6edd879aa48239f9a8a9016bef31d
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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