HCID 46945201, compound → HCID 59548023, compound

HRID 1946416Notes

Reaction equation

HRID 1946416 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[C:17](I)[CH:16]=[CH:15][C:14]=2[C:20]([F:23])([F:22])[F:21])[N:8]=1)=[O:5].[Cl-].[CH3:30][Zn+]>C1COCC1>[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[C:17]([CH3:30])[CH:16]=[CH:15][C:14]=2[C:20]([F:23])([F:22])[F:21])[N:8]=1)=[O:5]

Participants

4

Reactant 2

HCID 46945201HCID 46945201, compoundHCID 178477797HCID 178477797, compound

Product 1

HCID 59548023HCID 59548023, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 2,6-difluoro-N-(1-{[5-iodo-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)benzamide (for a preparation see Example 102)(80 mg, 0.158 mmol) in THF (1 ml) was added tetrakis(triphenyl-phosphine)palladium(0) (25 mg, 0.022 mmol, Aldrich). To the solution was added 2.0 M methylzinc chloride in THF (0.5 mL, 1.0 mmol, Aldrich) and the mixture stirred at 80° C. under nitrogen for 4 h. The solvent was removed in vacuo and the residue diluted with methanol:DMSO (1:1, 2 ml). The suspension was filtered and purified by MDAP on Sunfire C18 column (Method B) using Acetonitrile-Water with a Formic acid modifier. The solvent was evaporated in vacuo to give the title compound as a white solid (26.3 mg); LCMS: (System 4) MH+=396, tRET=3.00 min.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue diluted with methanol:DMSO (1:1, 2 ml)
  3. filtrationThe suspension was filtered
  4. custompurified by MDAP on Sunfire C18 column (Method B)
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-7326d1c0117d4e11ac52602be09fe233
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

Loading…