Toluene → HCID 58081337, compound

HRID 928375Notes

Reaction equation

HRID 928375 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]1.[N:11]1([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23]O)=[CH:19][C:18]=2[O:25][CH3:26])[CH:15]=[CH:14][CH:13]=[N:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.C([O-])(O)=O.[Na+]>C1COCC1>[N:11]1([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][N:1]3[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]3)=[CH:19][C:18]=2[O:25][CH3:26])[CH:15]=[CH:14][CH:13]=[N:12]1

Participants

7

Reactant 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 516892Sodium BicarbonateHCID 58081245HCID 58081245, compound

Product 1

HCID 58081337HCID 58081337, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of Ethyl 1H-pyrazole-4-carboxylate (117 mg, 0.833 mmol), crude (4-((1H-pyrazol-1-yl)methyl)-3-methoxyphenyl)methanol (256 mg, 71%, 0.833 mmol) and Triphenylphosphine (328 mg, 1.249 mmol) in THF (8 ml) DEAD 40% in Toluene (0.494 ml, 1.249 mmol) was added slowly at 0° C. The reaction mixture was stirred at 0° C. for 2 h and continued to stir for 12 h at rt. A saturated solution of NaHCO3 was added and the mixture was extracted with ethyl acetate. The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to afford crude Ethyl 1-(4-((1H-pyrazol-1-yl)methyl)-3-methoxybenzyl)-1H-pyrazole-4-carboxylate. MS [M+H]+=341.

Workup

  1. additionwas added slowly at 0° C
  2. stirringto stir for 12 h at rt
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eed554fd04dc477d9574c3ba3aecef6b
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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