HCID 21706292, compound → HCID 21706266, compound

HRID 1594899Notes

Reaction equation

HRID 1594899 reaction equation
[CH2:1]([C:4]1[C:9]([Br:10])=[CH:8][N:7]=[CH:6][C:5]=1[C:11]([C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([F:21])[CH:14]=1)=[O:12])[CH:2]=[CH2:3].[CH3:22][Mg]Br>C1COCC1>[CH2:1]([C:4]1[C:9]([Br:10])=[CH:8][N:7]=[CH:6][C:5]=1[C:11]([C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([F:21])[CH:14]=1)([OH:12])[CH3:22])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 21706292HCID 21706292, compoundHCID 178418573HCID 178418573, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 21706266HCID 21706266, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-allyl-5-bromo-pyridine-3-carbonyl)-2-fluoro-benzonitrile (as described above in Step C) (0.39 g, 1.13 mmol) in THF (20 mL) at 0° C. was added methylmagnesium bromide (1.13 mmol, 3M) and the reaction was monitored by TLC. Three more portions (1.13 mmol) of CH3MgBr were added until the reaction was complete. The reaction was quenched with saturated NH4Cl (20 mL), then partitioned between EtOAc and saturated NaHCO3. The organic layer was washed with brine and dried (MgSO4). Filtration and concentration to dryness gave the title compound after purification by chromatography on silica eluting with hexane:ethyl acetate 7:3.

Workup

  1. customThe reaction was quenched with saturated NH4Cl (20 mL)
  2. custompartitioned between EtOAc and saturated NaHCO3
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-7a4e40b8286e4266a1443f867c955a67
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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