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

HRID 1009538Notes

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

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, is heated with 1.5 mL of dimethylformamide dimethyl acetal and 100 μL pyrrolidine at 110° C. overnight. The DMF dimethyl acetal is removed in vacuo. The residue is redissolved in 3 mL of acetic acid, hydrazine hydrate (70 μL, 1.38 mmol) is added, and the mixture is heated to 100° C. for 2 h. The acetic acid is removed in vacuo, and the residue is partitioned between EtOAc and saturated NaHCO3. The organic phase is 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 gives a white crystalline powder.

Workup

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

Sources & evidence

ORD record: ord-b78920d80dd64063991a18c6e3126d59
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973069B2

Reaction notes

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