Cesium carbonate → HCID 57799866, compound

HRID 2101017Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH:14][C:15]2[CH:19]=[C:18]([CH3:20])[NH:17][N:16]=2)[N:3]=1.[NH2:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1.C([O-])([O-])=O.[Cs+].[Cs+].O1CCOCC1>CC([O-])=O.CC([O-])=O.[Pd+2].CN1CCCC1=O>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([NH:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1)=[N:3][C:4]([NH:14][C:15]1[CH:19]=[C:18]([CH3:20])[NH:17][N:16]=1)=[CH:5]2

Participants

Conditions

Temperature: 150 °C

Procedure

(1-chloro-6-methoxy-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine (100 mg), 4-amino-benzonitrile (85 mg), Cs2CO3 (376 mg), 2,2′-Bis(diphenylphosphino)-1′1-binaphthyl (BINAP) (44 mg), Pd(OAc)2 (8 mg), 1,4-dioxane (2 ml), N-methyl-pyrrolidone (NMP) (0.2 ml), were placed in a microwave bottle. The mixture was heated at 150° C. for 30 minutes under microwave irradiation and purified by preparative LC-MS to give 4-[6-methoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinolin-1-ylamino]-benzonitrile. LC-MS m/e 371 (MH+). 1H NMR(DMSO): δ 2.26(s, 3H), δ 3.86(s, 3H), δ 5.75(s, 1H), δ 6.52(m, 1H), δ 6.79(d, 1H), δ 7.12(s, 1H), δ 7.65(d, 2H), δ 8.20(m, 3H), δ 8.65(s,1H), δ 9.30(s, 1H), δ 11.75(s,1H).

Workup

custompurified by preparative LC-MS

Sources & evidence

ORD record: ord-0ed15bd9328b4c12b559f75601ac8e96
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572809B2

Reaction notes

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