1,3-diethyl-1H-indazole-6-carboxylic acid methoxy-methyl-amide → 1-(1,3-Diethyl-1H-indazol-6-yl)-ethanone

HRID 2240180Notes

Reaction equation

CON(C)[C:4]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH2:17][CH3:18])=[N:11][N:12]2[CH2:15][CH3:16])=[CH:8][CH:7]=1)=[O:5].[CH3:20][Mg]Cl>O1CCCC1>[CH2:15]([N:12]1[C:13]2[C:9](=[CH:8][CH:7]=[C:6]([C:4](=[O:5])[CH3:20])[CH:14]=2)[C:10]([CH2:17][CH3:18])=[N:11]1)[CH3:16]

Participants

Conditions

Temperature: -70 °C

Procedure

1,3-Diethyl-1H-indazole-6-carboxylic acid methoxy-methyl-amide (0.22 g, 0.86 mmol) was dissolved in tetrahydrofuran (8 mL) and cooled to −70° C. Methylmagnesium chloride (2 mL, 3M in tetrahydrofuran, 0.06 mol) was added dropwise and the resulting mixture was stirred for 30 minutes at −70° C. After warming to room temperature, the mixture was stirred for a further 3 minutes, then quenched by the addition of a chilled saturated solution of ammonium chloride. Ethyl acetate (150 mL) and water (40 mL) were then added and the product was extracted. The aqueous layer was re-extracted with ethyl acetate (75 mL). The organic layers were combined, dried, filtered, and concentrated to afford 200 mg of 1-(1,3-Diethyl-1H-indazol-6-yl)-ethanone.

Workup

temperatureAfter warming to room temperature
stirringthe mixture was stirred for a further 3 minutes
customquenched by the addition of a chilled saturated solution of ammonium chloride
additionEthyl acetate (150 mL) and water (40 mL) were then added
extractionthe product was extracted
extractionThe aqueous layer was re-extracted with ethyl acetate (75 mL)
customdried
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-4deaee25a1774a9a8fcd82031137a9f3
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723348B2

Reaction notes

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