Triethylamine → HCID 70648563, compound

HRID 868980Notes

Reaction equation

HRID 868980 reaction equation
Br[C:2]1[C:3]([CH3:10])=[N:4][CH:5]=[C:6]([CH3:9])[C:7]=1[NH2:8].[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH:12]=[CH2:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC>CN(C=O)C.O.C(O[Pd]OC(=O)C)(=O)C>[NH2:8][C:7]1[C:6]([CH3:9])=[CH:5][N:4]=[C:3]([CH3:10])[C:2]=1/[CH:13]=[CH:12]/[C:11]([O:15][CH2:16][CH3:17])=[O:14]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 11776TriphenylphosphineHCID 70097318HCID 70097318, compound

Product 1

HCID 70648563HCID 70648563, compoundYield 90.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-bromo-2,5-dimethylpyridin-4-amine (5.0 g, 25 mmol), ethyl acrylate (5.0 g, 50 mmol), diacetoxypalladium (1.12 g, 5.0 mmol), PPh3 (3.28 g, 12.5 mmol), and NEt3 (7.6 g, 75 mmol) in DMF (50 mL) was heated in a microwave reactor at 150° C. for 2 h. The reaction mixture was cooled, diluted with water (100 mL), and extracted with DCM (250 mL×3). The combined organic layers were washed with saturated sodium chloride solution (100 mL×3), dried with sodium sulfate, concentrated, and purified by column chromatography to give 5.0 g of the product as a yellow solid. MS (ESI): m/z 221.2 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with DCM (250 mL×3)
  3. washThe combined organic layers were washed with saturated sodium chloride solution (100 mL×3)
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-d15bff72932a435b94628bb21e625bc1
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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