Reaction equation
CON(C)[C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][N:7]=1)=[O:5].[CH3:16][Mg]Br.O.[Cl-].[NH4+]>O1CCCC1>[NH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([C:4](=[O:5])[CH3:16])=[N:7]1Participants
Conditions
- Temperature
- 0 °C
Procedure
In a round-bottomed flask, 2.4 g of N-methoxy-N-methyl-1H-indazole-3-carboxamide are placed in 140 ml of tetrahydrofuran at 0° C. and under argon. 19 ml of methylmagnesium bromide (3M in ethyl ether) are added dropwise. The mixture is stirred for one hour at 0° C. and 20 h at ambient temperature. It is cooled to 0° C. and 80 ml of water and 40 ml of a saturated solution of ammonium chloride are added. The mixture is extracted with 40 ml of ethyl acetate. The organic phase is washed with 40 ml of a saturated solution of sodium chloride, dried over magnesium sulphate and then concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a heptane/ethyl acetate mixture. 1.6 g of compound are obtained.
Workup
- temperatureIt is cooled to 0° C.
- extractionThe mixture is extracted with 40 ml of ethyl acetate
- washThe organic phase is washed with 40 ml of a saturated solution of sodium chloride
- dry with materialdried over magnesium sulphate
- concentrationconcentrated under reduced pressure
- customThe residue is purified by silica gel chromatography, elution
Sources & evidence
- ORD record
- ord-be03b3ea900a4de18284983fe9b1078b
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088765B2
Linked notes
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