HCID 12111719, compound → HCID 68839814, compound

HRID 660741Notes

Reaction equation

HRID 660741 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[CH:14]=[CH:13][CH:12]=[N:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[CH2:20]([O:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[N+:36]([O-:38])=[O:37])[CH:31]=[O:32])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[CH2:1]([O:8][CH2:9][N:10]1[C:14]([CH:31]([C:30]2[CH:33]=[CH:34][C:35]([N+:36]([O-:38])=[O:37])=[C:28]([O:27][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:29]=2)[OH:32])=[CH:13][CH:12]=[N:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 12111719HCID 12111719, compoundHCID 216869571-Benzyloxymethyl-1H-pyrazoleHCID 178418339Butyllithium

Product 1

HCID 68839814HCID 68839814, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-benzyloxymethyl-1H-pyrazole (Example 279, step A) (278 mg, 1.48 mmol) in THF (4 mL) at −78° C. is added n-BuLi (2.5 M in hexanes, 0.60 mL, 1.5 mmol) dropwise. The mixture is stirred at −78° C. for 20 min then a solution of 3-benzyloxy-4-nitrobenzaldehyde (Example 83, step A) (315 mg, 1.23 mmol) in THF (4 mL) is added dropwise. The mixture is stirred at −78° C. for 30 min and then is partitioned between EtOAc and aq. NH4Cl. The organic phase is dried over MgSO4 and concentrated. The crude material is chromatographed to afford the title compound as a light brown oil: (M+1)+=446, (M+HCO2−)=490.

Workup

  1. stirringThe mixture is stirred at −78° C. for 30 min
  2. customis partitioned between EtOAc and aq. NH4Cl
  3. dry with materialThe organic phase is dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude material is chromatographed

Sources & evidence

ORD record
ord-ec08297bf3724b2f8e357263a6b85849
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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