Potassium Carbonate → HCID 11578027, compound

HRID 1994545Notes

Reaction equation

HRID 1994545 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[C:30]3[CH:35]=[CH:34][C:33]([F:36])=[C:32](Cl)[CH:31]=3)[C@H:14]2[CH3:38])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[C:41](B(O)O)([CH3:43])=[CH2:42].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[C:30]3[CH:35]=[CH:34][C:33]([F:36])=[C:32]([C:41]([CH3:43])=[CH2:42])[CH:31]=3)[C@H:14]2[CH3:38])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10855372(Prop-1-en-2-yl)boronic acidHCID 11592442HCID 11592442, compound

Product 1

HCID 11578027HCID 11578027, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

In a tube was placed (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[3′-chloro-4′-fluoro-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one (Example 146) (30.2 mg, 0.0504 mmol), isopropenylboronic acid (27 mg, 0.31 mmol), 1,1-bis(di-t-butylphosphino)ferrocene palladium chloride (5.5 mg, 8.4×10−3 mmol), THF (350 μL) and 1 M aq. K2CO3 (350 μL). The tube was degassed with nitrogen, sealed, and heated at 100° C. for 5 hours. The reaction was then cooled to room temperature, diluted with EtOAc (50 mL) and washed with water and brine (15 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (0 to 15% EtOAc/hexanes) afforded (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[4′-fluoro-3′-isopropenyl-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one. Rf=0.29 (15% EtOAc/hexanes). LCMS=606.2 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.86 (s, 1H), 7.70 (s, 3H), 7.64 (d, J=8.0 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.23 (dd, J=7.8, 2.0 Hz, 1H), 7.12-7.17 (m, 2H), 5.54 (d, J=8.0 Hz, 1H), 5.28 (s, 1H), 5.26 (s, 1H), 4.90 (d, J=15.8 Hz, 1H), 4.18 (d, J=15.8 Hz, 1H), 3.78 (m, 1H), 2.16 (s, 3H), 0.47 (d, J=6.7 Hz, 3H).

Workup

  1. customIn a tube was placed
  2. customThe tube was degassed with nitrogen
  3. customsealed
  4. temperatureThe reaction was then cooled to room temperature
  5. additiondiluted with EtOAc (50 mL)
  6. washwashed with water and brine (15 mL each)
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification of the residue by flash chromatography on silica gel (0 to 15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-39a8923d5d0b45f8921f5a5f1ee3eefa
Source dataset
uspto-grants-2010_01
Patent number
US07652049B2

Reaction notes

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