Dimethylformamide → HCID 118162111, compound

HRID 1749457Notes

Reaction equation

HRID 1749457 reaction equation
Br[C:2]1[CH:17]=[CH:16][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][C:3]=1[O:18][C:19]([F:22])([F:21])[F:20].C(=O)([O-])O.[Na+].[CH3:28][N:29](C=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>[C:28]([C:2]1[CH:17]=[CH:16][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][C:3]=1[O:18][C:19]([F:22])([F:21])[F:20])#[N:29]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 118162178HCID 118162178, compound

Product 1

HCID 118162111HCID 118162111, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
160 °C

Procedure

A mixture of tert-butyl 4-bromo-3-(trifluoromethoxy)phenethylcarbamate (460 mg, 1.2 mmol), zinc cyanide (463 mg, 1.56 mmol) and tetrakis(triphenylphosphine)palladium (69 mg, 0.06 mmol) in DMF (10 mL) was stirred at 160° C. for 1 h under nitrogen. The reaction was treated with saturated sodium hydrogen carbonate and extracted with ethyl acetate (30 mL×3). The combined organic layers were washed with brine, dried, concentrated and purified by preparative thin layer chromatography (2.9% MeOH in DCM) to afford the title compound (150 mg, 0.45 mmol, 38% yield). MS (ESI) m/z 331.1 [M+1]+.

Workup

  1. extractionextracted with ethyl acetate (30 mL×3)
  2. washThe combined organic layers were washed with brine
  3. customdried
  4. concentrationconcentrated
  5. custompurified by preparative thin layer chromatography (2.9% MeOH in DCM)

Sources & evidence

ORD record
ord-1969d6335e90493bb81f29ba676fa1a6
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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