Potassium Phosphate, Tribasic → HCID 74220734, compound

HRID 2205836Notes

Reaction equation

[Cl:1][C:2]1[C:7](I)=[N:6][N:5]=[C:4]2[N:9]([CH3:18])[N:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:3]=12.[C:19]1(B2OC(C)(C)C(C)(C)O2)[CH2:23][CH2:22][CH2:21][CH:20]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.O.C(Cl)Cl>[Cl:1][C:2]1[C:7]([C:19]2[CH2:23][CH2:22][CH2:21][CH:20]=2)=[N:6][N:5]=[C:4]2[N:9]([CH3:18])[N:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:3]=12

Participants

Conditions

Temperature: 30 °C

Procedure

Nitrogen was bubbled through a suspension of 4-chloro-5-iodo-1-methyl-3-phenyl-pyrazolo[3,4-c]pyridazine (60 mg, 0.16 mmol), 2-(cyclopenten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (35 mg, 0.18 mmol) and K3PO4 (103 mg, 0.48 mmol) in DMF (1 mL) and water (0.3 mL) for 15 min. 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (13 mg, 0.016 mmol) was added and the tube sealed and heated to 30° C. for 16 h. The reaction mixture was diluted with CH2Cl2 and water. The aqueous phase was extracted with CH2Cl2 and the combined organic phases were dried (phase separator cartridge) and concentrated in vacuo. The resultant residue was purified using chromatography (silica gel, CH2Cl2/isohexane 1:1 to 1:0), to provide Compound IIIb as a solid (10 mg).

Workup

addition1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (13 mg, 0.016 mmol) was added
customthe tube sealed
extractionThe aqueous phase was extracted with CH2Cl2
customthe combined organic phases were dried (phase separator cartridge)
concentrationconcentrated in vacuo
customThe resultant residue was purified

Sources & evidence

ORD record: ord-59859404cff54349a245e54a3a6657ed
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371332B2

Reaction notes

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