Dimethylformamide → (5-methyl-1H-pyrazol-3-yl)-(1-phenyl-isoquinolin-3-yl)-amine

HRID 2100878

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH:12][C:13]2[CH:17]=[C:16]([CH3:18])[NH:15][N:14]=2)[N:3]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+].CN(C)C=O>O>[CH3:18][C:16]1[NH:15][N:14]=[C:13]([NH:12][C:4]2[N:3]=[C:2]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]3[C:6]([CH:5]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:17]=1

Participants

Conditions

Temperature: 180 °C

Procedure

The mixture of (1-chloro-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine (100 mg), phenylboronic acid (84 mg), Na2CO3 (145 mg), Tetrakis(triphenyl-phosphine)palladium(0) (40 mg), N,N-dimethylformamide (DMF) (1 ml) and water (1 ml) was heated at 180° C. for 30 minutes under microwave irradiation. After reaction finished, the reaction mixture was purified by preparative LC-MS to give (5-methyl-1H-pyrazol-3-yl)-(1-phenyl-isoquinolin-3-yl)-amine (40 mg). LC-MS m/e 301(MH+).+.) 1H NMR(CDCl3): δ 2.23(s, 3H), δ 5.86(s, 1H), δ 7.22(m, 1H), δ 7.40(m, 1H), δ 7.55(m, 5H), δ 7.70(m,4H), δ 7.90(d, 1H).

Workup

customAfter reaction
customthe reaction mixture was purified by preparative LC-MS

Sources & evidence

ORD record: ord-49008849975844d7a395efda69882188
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572809B2

Linked notes

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