Triethylamine → HCID 57293438, compound

HRID 1387455Notes

Reaction equation

HRID 1387455 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:16])[C:9]1[CH:14]=[CH:13][C:12](N)=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH:18]=[CH2:19].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CC#N.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:22]([O:21][C:17](=[O:20])[CH:18]=[CH:19][C:12]1[CH:11]=[N:10][C:9]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH3:16])=[CH:14][CH:13]=1)[CH3:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 21715784tert-Butyl (5-aminopyridin-2-yl)methylcarbamate

Product 1

HCID 57293438HCID 57293438, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 12-3 (6.0 g, 20.9 mmol), ethyl acrylate (6.3 mL, 62.7 mmol), triethylamine (17 mL, 125.5 mmol), tri-o-tolylphosphine (1.3 g, 6.2 mmol) and Pd(OAc)2 (0.5 g, 2.1 mmol) in 50 mL CH3CN was purged with argon for 5 min and subsequently refluxed at 110° C. for 20 hr. The mixture was cooled and concentrated. The residue was purified using silica gel flash chromatography (EtOAc/hexanes 1:3) to afford the desired product 12-4 as an oil.

Workup

  1. customwas purged with argon for 5 min
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. customThe residue was purified

Sources & evidence

ORD record
ord-484afbc9f4cb438c93e8a1afd229ef9e
Source dataset
uspto-grants-2001_07
Patent number
US06268378B1

Reaction notes

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