2-Methylphenylacetylene → HCID 58168216, compound

HRID 1029219Notes

Reaction equation

HRID 1029219 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][CH:22]=[CH:21][C:20]=1[CH3:25])#[CH:18]>>[CH3:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:17]#[C:18][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

Participants

3

Reactant 2

HCID 1365982-MethylphenylacetyleneHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

Product 1

HCID 58168216HCID 58168216, compoundYield 65.9%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 160 using 83 (100 mg, 0.43 mmol) and 2-ethynyltoluene (0.08 mL, 0.65 mmol) to provide 257 (88 mg, 65% yield) as a tan solid. LC-MS (M+H=311 obsd.=311). 1H NMR (400 MHz, d6-DMSO): δ 9.79 (d, 1H), 8.48 (d, 1H), 8.42 (dd, 1H), 7.95 (m, 1H), 7.75 (m, 2H), 7.46 (m, 3H), 7.36 (m, 1H), 2.61 (s, 3H).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-b82dd52614fe48fa9ea9881912dce617
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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