Dichloromethane → {4-[6-(2,6-dichloro-3,5-dimethoxyphenyl)-1H-pyrazolo[4,3-c]pyridin-3-yl]-1H-pyrazol-1-yl}acetic acid

HRID 1778706Notes

Reaction equation

[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[N:18]=[CH:17][C:16]2[C:19](I)=[N:20][NH:21][C:15]=2[CH:14]=1.C([O:25][C:26](=[O:42])[CH2:27][N:28]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=[N:29]1)C.ClCCl.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[N:18]=[CH:17][C:16]2[C:19]([C:31]3[CH:30]=[N:29][N:28]([CH2:27][C:26]([OH:42])=[O:25])[CH:32]=3)=[N:20][NH:21][C:15]=2[CH:14]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[4,3-c]pyridine (0.20 g, 0.44 mmol), ethyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]acetate (Aldrich, Cat. No. 683566) (0.14 g, 0.49 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (18 mg, 0.022 mmol), and potassium carbonate (0.184 g, 1.33 mmol) in 1,4-dioxane (10 mL) and water (5 mL) was degassed and recharged with nitrogen three times. The reaction mixture was stirred at 85° C. for 6 h. The reaction mixture was adjusted to pH˜4 with 1N HCl. The precipitates formed were filtered, washed with water and ether, and dried under vacuum to afford the desired product (0.10 g, 50%). LCMS (M+H)+=448.0/450.0.

Workup

customwas degassed
customThe precipitates formed
filtrationwere filtered
washwashed with water and ether
customdried under vacuum

Sources & evidence

ORD record: ord-c3bc0292cb754f9d885736d5200d3cc7
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266892B2

Reaction notes

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