Triethylamine → HCID 70648565, compound

HRID 868983Notes

Reaction equation

HRID 868983 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([CH3:13])[CH:6]=[N:7][C:8]=2[CH3:12])[N:3]=1.[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[CH:15]=[CH2:16].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC>CN(C)C=O.O.C(O[Pd]OC(=O)C)(=O)C>[CH3:12][C:8]1[N:7]=[CH:6][C:5]([CH3:13])=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2](/[CH:16]=[CH:15]/[C:14]([O:18][CH2:19][CH3:20])=[O:17])=[N:3]2

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 11776TriphenylphosphineHCID 86687897HCID 86687897, compound

Product 1

HCID 70648565HCID 70648565, compoundYield 86.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-bromo-5,8-dimethyl-1,6-naphthyridine (0.63 g, 2.7 mmol), ethyl acrylate (0.53 g, 5.4 mmol), diacetoxypalladium (121 mg, 0.5 mmol), PPh3 (0.35 g, 1.4 mmol), and NEt3 (0.82 g, 8.1 mmol) in N,N-dimethylformamide (5 mL) was heated in a microwave reactor at 150° C. for 1 h. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (50 mL×3). The combined organic layers were washed with saturated sodium chloride solution (50 mL×3), dried with sodium sulfate and concentrated to give 0.6 g of the crude product as a yellow solid, which was used for the next step without further purification. MS (ESI): m/z 257.1 [M+H]+.

Workup

  1. extractionextracted with EtOAc (50 mL×3)
  2. washThe combined organic layers were washed with saturated sodium chloride solution (50 mL×3)
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-071be9809a4f446e9fd0ade027ef8e92
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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