Ethyl Acetate → HCID 11384091, compound

HRID 403041Notes

Reaction equation

HRID 403041 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][OH:8].[H-].[Na+].Cl[C:12]1[CH:33]=[CH:32][C:15]([C:16]([NH:18][C:19]2[CH:24]=[C:23]([C:25]([NH:27][CH:28]3[CH2:30][CH2:29]3)=[O:26])[CH:22]=[CH:21][C:20]=2[CH3:31])=[O:17])=[CH:14][N:13]=1.C(OCC)(=O)C>N1C(C)=CC(C)=CC=1C.[Cu]I>[CH:28]1([NH:27][C:25]([C:23]2[CH:22]=[CH:21][C:20]([CH3:31])=[C:19]([NH:18][C:16](=[O:17])[C:15]3[CH:32]=[CH:33][C:12]([O:8][CH2:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[N:13][CH:14]=3)[CH:24]=2)=[O:26])[CH2:30][CH2:29]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11474PiconolHCID 24758Sodium hydrideHCID 59761511HCID 59761511, compound

Product 1

HCID 11384091HCID 11384091, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 79532,4,6-TrimethylpyridineSolvent

Procedure

To 2-pyridinylmethanol (1 mL) was added sodium hydride 60% dispersion in oil (122 mg, 3.05 mmol) under inert atmosphere and the resulting mixture was stirred for 10 minutes then added to a mixture of 6-chloro-N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}nicotinamide (334 mg, 1.02 mmol) and copper (I) iodide in collidine (3 mL). The resulting mixture was stirred at room temperature for 30 minutes then at 100° C. for 4 h. The mixture was cooled to room temperature, ethyl acetate was added and the mixture filtered. The filtrates were concentrated under reduced pressure and purified by silica column chromatography eluting with 0 to 100% ethyl acetate in isohexane. Trituration with diethyl ether gave the title compound as a colourless solid (105.6 mg, 26%); NMR Spectrum: (DMSOd6) 0.59 (m, 2H), 0.67-0.71 (m, 2H), 2.27 (s, 3H), 2.86 (m, 1H), 5.53 (s, 2H), 7.10 (d, 1H), 7.35 (m, 2H), 7.48 (m, 1H), 7.65 (m, 1H), 7.82 (m, 2H), 8.29 (m, 1H), 8.37 (m, 1H), 8.58 (m, 1H), 8.80 (d, 1H), 9.99 (s, 1H); Mass Spectrum: M+H+ 403.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 30 minutes
  2. waitat 100° C. for 4 h
  3. filtrationthe mixture filtered
  4. concentrationThe filtrates were concentrated under reduced pressure
  5. custompurified by silica column chromatography
  6. washeluting with 0 to 100% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-17b4a145a75541b99d6a6e98f12e041e
Source dataset
uspto-grants-2014_06
Patent number
US08742124B2

Reaction notes

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