1-Ethynyl-4-methoxybenzene → HCID 58168239, compound

HRID 1029132Notes

Reaction equation

HRID 1029132 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.[C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)#[CH:18]>CCOC(C)=O.O>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]#[C:18][C:2]2[CH:11]=[CH:10][N:9]=[C:8]3[C:3]=2[C:4]2[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=2[C:6](=[O:12])[NH:7]3)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 2510201-Ethynyl-4-methoxybenzeneHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

Product 1

HCID 58168239HCID 58168239, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Conditions

Temperature
100 °C

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 160 using Compound 83 (100 mg, 0.43 mmol) and 1-Ethynyl-4-methoxy-benzene (86 mg, 0.65 mmol) was then added, and the resulting solution was stirred for 3 h at 100° C. The reaction mixture was diluted with EtOAc/H2O. The resulting precipitate was filtered, washed with EtOAc/H2O, and dried under vacuum to provide 163 (101 mg, 71% yield) as a white solid. LC-MS (M+H=327, obsd.=327).

Workup

  1. customThe title compound was synthesized
  2. additionwas then added
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with EtOAc/H2O
  5. customdried under vacuum

Sources & evidence

ORD record
ord-00294db3f784421d90ef8fc990922531
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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