Potassium Carbonate → HCID 24969552, compound

HRID 1508595Notes

Reaction equation

HRID 1508595 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.C(=O)([O-])[O-].[K+].[K+].[F:37][C:38]1[C:43]([CH:44]([CH3:46])[CH3:45])=[CH:42][C:41](B(O)O)=[C:40]([O:50][CH3:51])[CH:39]=1>C1COCC1>[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:41]4[CH:42]=[C:43]([CH:44]([CH3:46])[CH3:45])[C:38]([F:37])=[CH:39][C:40]=4[O:50][CH3:51])=[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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53363739(4-Fluoro-5-isopropyl-2-methoxyphenyl)boronic acid2×HCID 57576268(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[(3-bromo-6-chloropyridin-2-yl)methyl]-4-methyl-1,3-oxazolidin-2-one2×

Product 1

HCID 24969552HCID 24969552, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
32 °C

Procedure

To (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[(3-bromo-6-chloropyridin-2-yl)methyl]-4-methyl-1,3-oxazolidin-2-one (INTERMEDIATE 32) (460 mg, 0.889 mmol) in THF (10 mL) was added potassium carbonate (2 M in water, 1.3 mL, 2.67 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (57.9 mg, 0.089 mmol) and (4-fluoro-5-isopropyl-2-methoxyphenyl)boronic acid (INTERMEDIATE 59) (283 mg, 1.33 mmol). The reaction was degassed with nitrogen and heated at 32° C. for 16 hr. The reaction was then poured into brine and extracted with ethyl acetate (2×10 mL). The combined extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified via flash chromatography on silica gel to afford (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-({6-chloro-3-[4-fluoro-2-methoxy-5-(propan-2-yl)phenyl]pyridin-2-yl}methyl)-4-methyl-1,3-oxazolidin-2-one (419.4 mg, 0.693 mmol) LCMS calc.=605.1. found=605.1.

Workup

  1. customThe reaction was degassed with nitrogen
  2. additionThe reaction was then poured into brine
  3. extractionextracted with ethyl acetate (2×10 mL)
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via flash chromatography on silica gel

Sources & evidence

ORD record
ord-e299c2b4091444cfbadde42500dc74ea
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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