tert-Butyl acrylate → HCID 86590075, compound

HRID 1370580Notes

Reaction equation

HRID 1370580 reaction equation
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:10]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])[CH:11]=[CH2:12].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:9][C:3]1[C:2](/[CH:12]=[CH:11]/[C:10]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:7][C:6]([Cl:8])=[CH:5][N:4]=1

Participants

6

Reactant 3

HCID 15458tert-Butyl acrylateHCID 80271Tri-o-tolylphosphineHCID 27639713-Bromo-5-chloropyridin-2-amine

Product 1

HCID 86590075HCID 86590075, compoundYield 44.9%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-bromo-5-chloro-2-pyridinamine (C. W. Murtiashaw, R. Breitenbach, S. W. Goldstein, S. L. Pezzullo, J. Quallich, R. Sarges, J. Org. Chem., 1992, 57, 1930) (8.56 g, 41.4 mmol), t-butyl acrylate (12 ml, 82 mmol), tri-o-tolylphosphine (2.92 g. 9.6 mmol) and palladium acetate (540 mg, 2.4 mmol) in triethylamine (130 ml) was heated in a sealed bomb to 150° C. for 10 hours. The reaction mixture was filtered, the residue washed with EtOAc and the combined filtrates evaporated to a dark brown oil. Purification by column chromatography upon silica gel using hexane—EtOAc (7:3) as eluant and subsequent crystallisation from hexane at −78° C. gave the title compound as a bright yellow solid (4.75 g, 18.6 mmol).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe residue washed with EtOAc
  3. customthe combined filtrates evaporated to a dark brown oil
  4. customPurification by column chromatography upon silica gel
  5. customsubsequent crystallisation from hexane at −78° C.

Sources & evidence

ORD record
ord-9d93a99a700a4a2c9a2fd7e3055d29cf
Source dataset
uspto-grants-2003_06
Patent number
US06583162B1

Reaction notes

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