Ethyl Acetate → HCID 118045363, compound

HRID 595977Notes

Reaction equation

HRID 595977 reaction equation
Br[C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[N:10]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:5]=[C:6]([F:8])[CH:7]=1.CCN(C(C)C)C(C)C.[CH3:32][S-:33].[Na+].CCOC(C)=O>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[F:8][C:6]1[CH:5]=[C:4]([C@H:9]2[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[N:10]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:3]=[C:2]([S:33][CH3:32])[CH:7]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 4378561Sodium methanethiolateHCID 118054559HCID 118054559, compound

Product 1

HCID 118045363HCID 118045363, compoundYield 102%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of Xantphos (13.91 mg, 0.024 mmol), Pd2(dba)3 (22.02 mg, 0.024 mmol), (5)-tert-butyl 4-(3-bromo-5-fluorophenyl)-2,2-dimethyloxazolidine-3-carboxylate (300 mg, 0.802 mmol), DIEA (700 μl, 4.01 mmol) and sodium methanethiolate (112 mg, 1.603 mmol) in toluene (2.6 mL) was microwave heated at 110° C. for 18 min. EtOAc was added, and washed with sat NaHCO3, water, and brine. The mixture was filtered off, concentrated and purified with flash chromatography eluting with 0-60% of EtOAc/heptane to provide (S)-tert-butyl 4-(3-fluoro-5-(methylthio)phenyl)-2,2-dimethyloxazolidine-3-carboxylate (278 mg, 102%) as an oil. LCMS (m/z): 286.1 (MH+-56), 1.14 min.

Workup

  1. washwashed
  2. filtrationThe mixture was filtered off
  3. concentrationconcentrated
  4. custompurified with flash chromatography
  5. washeluting with 0-60% of EtOAc/heptane

Sources & evidence

ORD record
ord-6a49e12b1aa64551aeaabd25e8069136
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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