Toluene → HCID 66723638, compound

HRID 928450Notes

Reaction equation

HRID 928450 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11]O)=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH3:13].[NH:14]1[CH:18]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:16]=[N:15]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:14]3[CH:18]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:16]=[N:15]3)=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH3:13]

Participants

5

Reactant 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 58081233HCID 58081233, compound

Product 1

HCID 66723638HCID 66723638, compound

Procedure

To a solution of (1,2-Dimethyl-1H-indol-5-yl)methanol (crude, 250 mg, 76%, 1.084 mmol), Ethyl 1H-pyrazole-4-carboxylate (266 mg, 1.898 mmol) and Triphenylphosphine (341 mg, 1.3 mmol) in toluene (10.5 ml) Diethyl azodicarboxylate (206 ul, 1.3 mmol) was added at rt. The reaction mixture was stirred at rt for 16 hours. The reaction mixture was quenched with brine and extracted twice with DCM. The combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum. The crude product was purified by flash-chromatography on silica gel (60 g), gradient of cyclohexane/EA (50 ml/min.) from 100/0 (3 min.) to 70/30 (20 min.) to afford pure ethyl 1-((1,2-dimethyl-1H-indol-5-yl)methyl)-1H-pyrazole-4-carboxylate. MS (Method V) [M+H]+=298.4.

Workup

  1. customThe reaction mixture was quenched with brine
  2. extractionextracted twice with DCM
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by flash-chromatography on silica gel (60 g), gradient of cyclohexane/EA (50 ml/min.) from 100/0 (3 min.) to 70/30 (20 min.)

Sources & evidence

ORD record
ord-89332359aad94bc5bb0d94536cdb2c25
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

Loading…