Triethylamine → HCID 86665132, compound

HRID 1842035Notes

Reaction equation

HRID 1842035 reaction equation
[Br:1][C:2]1[N:7]=[C:6](I)[C:5]([NH2:9])=[CH:4][CH:3]=1.[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=[CH2:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C(#N)C>[CH2:15]([O:14][C:10](=[O:13])/[CH:11]=[CH:12]/[C:6]1[C:5]([NH2:9])=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=1)[CH3:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 11776TriphenylphosphineHCID 534011776-Bromo-2-iodopyridin-3-amine

Product 1

HCID 86665132HCID 86665132, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

15.5 g 6-Bromo-2-iodo-pyridin-3-ylamine, 5.9 ml ethyl acrylate, 2.72 g triphenylphosphine and 28.75 ml triethylamine were dissolved in 90 ml acetonitrile. An argon stream was bubbled through the reaction mixture for 10 minutes then 2.33 g palladium(II)acetate were added and the reaction mixture stirred at 80° C. The reaction mixture was filtered hot trough a pad of celite then the solvent was removed in vacuo. The residue was purified by chromatography on silica gel to obtain 10.2 g (E)-3-(3-Amino-6-bromo-pyridin-2-yl)-acrylic acid ethyl ester.

Workup

  1. customAn argon stream was bubbled through the reaction mixture for 10 minutes
  2. addition2.33 g palladium(II)acetate were added
  3. filtrationThe reaction mixture was filtered hot trough a pad of celite
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-4db0bf72d4ad4e9b9f5bd42ee950c8d3
Source dataset
uspto-grants-2015_02
Patent number
US08946212B2

Reaction notes

Loading…