Potassium Carbonate → Methyl 2-(3-acetyl-5-(benzyloxy)-1H-indazol-1-yl)acetate

HRID 1052101Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[C:12]2[C:18](=[O:20])[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:28][C:29]([O:31][CH3:32])=[O:30]>CC#N>[C:18]([C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=2)[N:14]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[N:13]=1)(=[O:20])[CH3:19]

Participants

Conditions

Temperature: 90 °C

Procedure

To 1-(5-(benzyloxy)-1H-indazol-3-yl)ethanone (3.50 g, 13.1 mmol) in CH3CN (100 mL) was added K2CO3 (4.54 g, 32.9 mmol) and methyl 2-bromoacetate (1.33 mL, 14.5 mmol). The reaction mixture was stirred at 90° C. for 90 min. Then was filtered and the residue was washed with CH3CN. Volatiles were evaporated and the crude mixture was purified by flash column chromatography on silica gel (c-hexane/EtOAc 1:1 to 1:3). TLC, Rf (c-hexane/EtOAc 1:3)=0.64; MS (LC/MS): 339.0 [M+H]+, 361.0 [M+Na]+; tR (HPLC conditions e): 5.09 min.

Workup

filtrationThen was filtered
washthe residue was washed with CH3CN
customVolatiles were evaporated
customthe crude mixture was purified by flash column chromatography on silica gel (c-hexane/EtOAc 1:1 to 1:3)
custom5.09 min.

Sources & evidence

ORD record: ord-7b0246c3f2c14467bf62242c6604fb29
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388199B2

Reaction notes

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