Cesium carbonate → HCID 178522297, compound

HRID 449875Notes

Reaction equation

[Cl:1][C:2]1[CH:16]=[C:15](I)[CH:14]=[C:13]([Cl:18])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)=[O:5].CC1(C)C(C)(C)OB([C:27]2[CH:28]=[N:29][NH:30][CH:31]=2)O1.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[CH:16]=[C:15]([C:28]2[CH:27]=[CH:31][NH:30][N:29]=2)[CH:14]=[C:13]([Cl:18])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)=[O:5]

Participants

Conditions

Temperature: 160 °C

Procedure

To the solution of 2,6-dichloro-4-iodo-N-(pyridin-4-yl)benzamide (0.17 g, 0.43 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.125 g, 0.65 mmol), Cs2CO3 (0.28 g, 0.86 mmol) in CH3CN/H2O (1 mL/1 mL) was added PdCl2(dppf) (31 mg, 0.043 mmol) under N2 atmosphere. The mixture was heated at 160° C. under the irradiation of microwave for 30 minutes. After the completion of the reaction, the mixture was filtered through Celite and purified by preparative basic HPLC (Gemini, 200 mm×25 mm, gradient: CH3CN/0.05% NH3.H2O, 50-80, 10 min) to afford the desired product (23.8 mg, 17% yield). 1HNMR (DMSO-d6, 400 MHz): 611.19 (s, 1H), 8.49 (s, 2H), 8.29 (s, 2H), 7.88 (s, 2H), 7.65 (s, 2H), 7.07 (s, 1H). LCMS (ESI) m/z: 333.1 [M+H+]

Workup

customAfter the completion of the reaction
filtrationthe mixture was filtered through Celite
custompurified by preparative basic HPLC (Gemini, 200 mm×25 mm, gradient: CH3CN/0.05% NH3.H2O, 50-80, 10 min)

Sources & evidence

ORD record: ord-0546fa5307b945c6b7871011b1c2bc8a
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486950B2

Reaction notes

Loading…