Dimethylformamide → HCID 66576889, compound

HRID 1775545Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][N:5]=[C:4]2[N:14]([CH3:24])[N:15]=[C:16]([C:17]3[CH:22]=[CH:21][C:20](I)=[CH:19][CH:18]=3)[C:3]=12.[CH3:25][N:26](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][N:5]=[C:4]2[N:14]([CH3:24])[N:15]=[C:16]([C:17]3[CH:22]=[CH:21][C:20]([C:25]#[N:26])=[CH:19][CH:18]=3)[C:3]=12

Participants

Conditions

Temperature: 100 °C

Procedure

A degassed mixture of 4-chloro-3-(4-iodophenyl)-1-methyl-5-phenyl-1H-pyrazolo[3,4-c]pyridazine (Compound 43, Example 23) (70 mg, 0.16 mmol), Zn(CN)2 (18 mg, 0.094 mmol) and Pd(PPh3)4 (18 mg, 0.016 mmol) in DMF (1 mL) was heated at 100° C. for 40 min in a microwave. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried using a phase separating cartridge and concentrated in vacuo. The crude residue was purified by column chromatography (silica gel, 10 to 20% ethyl acetate/isohexane), yielding Compound 24 as a solid (30 mg).

Workup

customThe reaction mixture was partitioned between ethyl acetate and water
washThe organic phase was washed with water and brine
customdried
customseparating cartridge
concentrationconcentrated in vacuo
customThe crude residue was purified by column chromatography (silica gel, 10 to 20% ethyl acetate/isohexane)

Sources & evidence

ORD record: ord-43c2cedd21394bc7a9037dea7b293a8a
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260381B2

Reaction notes

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