HCID 68774908, compound → HCID 57543438, compound

HRID 2261263Notes

Reaction equation

HRID 2261263 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[C:9]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]2[N:17]([C:20]3[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=3[F:27])[N:18]=[CH:19][C:11]=2[CH:10]=1.[Cu][C:29]#[N:30]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:29]#[N:30])=[CH:4][C:3]=1[C:9]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]2[N:17]([C:20]3[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=3[F:27])[N:18]=[CH:19][C:11]=2[CH:10]=1

Participants

4

Reactant 2

HCID 68774908HCID 68774908, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 57543438HCID 57543438, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-(2-chloro-5-iodophenyl)-1-(2,6-difluorophenyl)-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (60 mg, 0.12 mmol) and copper(I) cyanide (54 mg, 0.6 mmol) in DMF (1.5 mL) were heated in a microwave at 140° C. for 1 h. LC-MS indicates ˜60% conversion to the desired product. Additional copper(I) cyanide (100 mg) was added and the reaction mixture was heated for another 1 h in the microwave at 140° C. The reaction mixture was diluted in DCM (20 mL), washed with brine (2×15 mL), dried over MgSO4, filtered and concentrated. The crude residue was purified on the ISCO 12 g column (15-50% EtOAc in hexanes) affording the title compound as a white amorphous solid. MS (ESI, pos.ion) m/z: 397.0 (M+1).

Sources & evidence

ORD record
ord-579b88c919554d2494289e8a7a461943
Source dataset
uspto-grants-2010_12
Patent number
US07846944B2

Reaction notes

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