Potassium Carbonate → Methyl 3-{3-[4-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(methylsulfanyl)pyrimidin-5-yl]-4-methoxyphenyl}propanoate

HRID 1508568Notes

Reaction equation

HRID 1508568 reaction equation
[F:1][C:2]([F:31])([F:30])[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][N:23]=[C:22]([S:27][CH3:28])[N:21]=3)[C@H:14]2[CH3:29])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][C:42]([O:44][CH3:45])=[O:43])=[CH:36][C:35]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[F:1][C:2]([F:31])([F:30])[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:39]4[CH:38]=[C:37]([CH2:40][CH2:41][C:42]([O:44][CH3:45])=[O:43])[CH:36]=[CH:35][C:34]=4[O:33][CH3:32])=[CH:24][N:23]=[C:22]([S:27][CH3:28])[N:21]=3)[C@H:14]2[CH3:29])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 57576287(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-{[5-bromo-2-(methylthio)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one2×HCID 67036621Methyl 3-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate2×

Product 1

HCID 86704617Methyl 3-{3-[4-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(methylsulfanyl)pyrimidin-5-yl]-4-methoxyphenyl}propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5-bromo-2-(methylsulfanyl)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one (INTERMEDIATE 45) (307 mg, 0.579 mmol), methyl 3-[4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate (INTERMEDIATE 2) (185 mg, 0.579 mmol), 1,1bis(di-tert-butylphosphino)ferrocene palladium dichloride (39.4 mg, 0.058 mmol), potassium carbonate (0.724 ml, 1.447 mmol) and THF (5 mL) were sealed in a uw vessel and subject to microwave irradiation at 140° C. for 20 min. The reaction crude was dried over Na2SO4, filtered and purified by preparative TLC (silica gel) developed with EtOAc/hexanes (40% ethyl acetate v/v) to give a brown solid as the titled compound. LCMS calc.=643.16. found=644.17 (M+H)+.

Workup

  1. customsubject to microwave irradiation at 140° C. for 20 min
  2. customThe reaction crude
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. custompurified by preparative TLC (silica gel)

Sources & evidence

ORD record
ord-a3630d5cf53e43dc9d45beed64c61dcf
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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