Dimethylformamide → HCID 25028948, compound

HRID 1436364Notes

Reaction equation

HRID 1436364 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:13]3[C@H:17]([CH2:18][CH3:19])[CH2:16][O:15][C:14]3=[O:20])[S:11][CH:12]=2)=[CH:4][CH:3]=1.[CH3:21][N:22](C=O)C>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:18]([C@@H:17]1[CH2:16][O:15][C:14](=[O:20])[N:13]1[C:10]1[S:11][CH:12]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:21]#[N:22])=[CH:3][CH:4]=2)[N:9]=1)[CH3:19]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 25028946HCID 25028946, compound

Product 1

HCID 25028948HCID 25028948, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
145 °C

Procedure

To a solution of (4R)-3-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-4-ethyl-1,3-oxazolidin-2-one (1.46 g, 4.13 mmol), prepared in step 2 of Example 9, in dry DMF (15 mL) was added zinc cyanide (0.266 g, 2.27 mmol) and tetrakis(triphenylphosphine)palladium (0) (150 mg), under nitrogen, and the mixture heated to 145° C. After 1 h, the mixture was cooled to room temperature, diluted with ethyl acetate, which was then washed with water, brine, dried (anhydrous sodium sulfate) and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate:hexanes, gradient elution) to afford the title compound (0.67 g, 54%), mp 153-157° C., MS m/z 300 [M+H]+. ANLC 100% at 210-370 nm, 9.5 min; 100% at 240 nm, 9.5 min, Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. washwas then washed with water, brine
  3. dry with materialdried (anhydrous sodium sulfate)
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexanes, gradient elution)

Sources & evidence

ORD record
ord-6bae271b9c8d41b7a3200b0c477f3447
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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