HCID 67120074, compound → HCID 67120050, compound

HRID 1410150Notes

Reaction equation

HRID 1410150 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N:10]1[C:14](I)=[C:13]([C:16]#[N:17])[C:12]([CH3:18])=[N:11]1.[Li]CCCC.CON(C)[C:27](=[O:36])[CH:28]([CH3:35])[CH2:29][CH:30]([O:33][CH3:34])[O:31][CH3:32]>CCOCC>[CH3:32][O:31][CH:30]([O:33][CH3:34])[CH2:29][CH:28]([CH3:35])[C:27]([C:14]1[N:10]([C:3]2[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=2[F:1])[N:11]=[C:12]([CH3:18])[C:13]=1[C:16]#[N:17])=[O:36]

Participants

5

Reactant 3

HCID 67120074HCID 67120074, compoundHCID 86668980HCID 86668980, compoundHCID 178418339Butyllithium

Product 1

HCID 67120050HCID 67120050, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-40 °C

Procedure

To 1-(2-fluoro-4-methoxyphenyl)-5-iodo-3-methyl-1H-pyrazole-4-carbonitrile (66 mg, 0.18 mmol) in Et2O (1.5 mL) at −78° C. was added n-BuLi (2.5 M solution in hexane, 0.1 mL, 0.24 mmol). After stirring for 15 min, N,4,4-trimethoxy-N,2-dimethylbutanamide was added in Et2O (1.5 mL). The reaction was stirred at −78° C. for 15 hours while warming to −40° C. The reaction was quenched with water and extracted using a mixture of Et2O and DCM. Drying using a phase separator followed by concentration and purification using silica gel (heptane-EtOAc, 1:0 to 0:1) afforded 5-(4,4-dimethoxy-2-methylbutanoyl)-1-(2-fluoro-4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (33 mg, 48%).

Workup

  1. stirringThe reaction was stirred at −78° C. for 15 hours
  2. customThe reaction was quenched with water
  3. extractionextracted
  4. additiona mixture of Et2O and DCM
  5. customDrying
  6. concentrationfollowed by concentration and purification

Sources & evidence

ORD record
ord-c17a1629901140dea1108df576bd6c59
Source dataset
uspto-grants-2014_12
Patent number
US08921402B2

Reaction notes

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