Cesium carbonate → HCID 86662436, compound

HRID 2368166Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)=[O:9].C[C:24]1([CH3:33])[CH:29]=[CH:28][CH:27]=[C:26](B(O)O)[CH2:25]1.[C:34]([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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[N:3]=[N:4][C:5]([C:28]2[CH:29]=[C:24]([CH3:33])[CH:25]=[C:26]([CH3:34])[CH:27]=2)=[CH:6][C:7]=1[C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 3,6-dichloro-N-(3,4-dimethoxybenzyl)pyridazine-4-carboxamide (1-2, 0.100 g, 0.292 mmol, 1.0 equiv), 3,3-dimethylphenylboronic acid (0.053 g, 0.351 mmol, 1.2 equiv), Cs2CO3 (0.238 g, 0.731 mmol, 2.5 equiv) and PdCl2(dppf) (0.043 g, 0.058 mmol, 0.2 equiv) was made in dioxane (2.0 mL) and heated to 80° C. for 2 hours. The reaction mixture was cooled and partitioned between EtOAc and water. The organic phase was dried over MgSO4 and concentrated. The residue was purified by normal phase column chromatography (0 to 85% EtOAc in hexanes) to afford the product (1-3) as a solid. ESI+MS [M+H]+ C22H22ClN3O3: 412.1 found, 412.1 required.

Workup

temperatureThe reaction mixture was cooled
custompartitioned between EtOAc and water
dry with materialThe organic phase was dried over MgSO4
concentrationconcentrated
customThe residue was purified by normal phase column chromatography (0 to 85% EtOAc in hexanes)

Sources & evidence

ORD record: ord-53d359fb281e4d6792da9912a8a8b823
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703770B2

Reaction notes

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