Hydrazine hydrate (1:1) → HCID 11680306, compound

HRID 907109Notes

Reaction equation

HRID 907109 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14](=O)[CH3:15])=[CH:4]1)[CH3:2].C([N:19]1[C:27]2C(=CC=C(OC)C=2)C=C1)C.COC(OC)[N:33](C)C.O.NN>N1CCCC1>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]2[NH:33][N:19]=[CH:27][CH:15]=2)=[CH:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 59425473HCID 59425473, compoundHCID 59425954HCID 59425954, compound

Product 1

HCID 11680306HCID 11680306, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 31268PyrrolidineSolvent

Conditions

Temperature
100 °C

Procedure

1-(1-Ethyl-6-methoxy-1H-indol-3-yl)-ethanone (100 mg, 0.46 mmol), prepared from 1-ethyl-6-methoxy-1H-indole by the procedure described in example 1L, was heated with 1.5 mL of dimethylformamide dimethyl acetal and 100 μL pyrrolidine at 110° C. overnight. The DMF dimethyl acetal was removed in vacuo. The residue was redissolved in 3 mL of acetic acid, hydrazine hydrate (70 μL, 1.38 mmol) was added, and the mixture was heated to 100° C. for 2 h. The acetic acid was removed in vacuo, and the residue was partitioned between EtOAc and saturated NaHCO3. The organic phase was dried and concentrated and the product purified by silica gel chromatography (EtOAc/Hex, 1/1) to give 59 mg of 1-ethyl-6-methoxy-3-(2H-pyrazol-3-yl)-1H-indole (54%) as a colorless semisolid. Trituration in Et2O gave a white crystalline powder.

Workup

  1. customThe DMF dimethyl acetal was removed in vacuo
  2. dissolutionThe residue was redissolved in 3 mL of acetic acid
  3. customThe acetic acid was removed in vacuo
  4. customthe residue was partitioned between EtOAc and saturated NaHCO3
  5. customThe organic phase was dried
  6. concentrationconcentrated
  7. customthe product purified by silica gel chromatography (EtOAc/Hex, 1/1)

Sources & evidence

ORD record
ord-76fe3c556e424629a39681f0103d031e
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

Loading…