HCID 11312687, compound → HCID 22480369, compound

HRID 1275715Notes

Reaction equation

HRID 1275715 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH2:5]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]2[O:22][C:23]([CH:26]=[O:27])=[CH:24][CH:25]=2)=[N:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1COCC1.C(OCC)C>[CH2:5]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]2[O:22][C:23]([CH:26]([OH:27])[CH2:1][CH3:2])=[CH:24][CH:25]=2)=[N:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 11312687HCID 11312687, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 22480369HCID 22480369, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

At 10° C., 1.1 ml (1.1 mmol) of a 1M solution of ethylmagnesium bromide in THF were added dropwise to 300 mg (0.99 mmol) of 1-benzyl-3-(5-formyl-2-furyl)indazole in 20 ml of diethyl ether. After 1 h at 10° C., the mixture was poured into ice-water and extracted with ethyl acetate, dried and concentrated. The crude product was purified by silica gel chromatography using dichloromethane/methanol (95:5). This gave 200 mg (61%) of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. customdried
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-988944550b174d6fb7587d28ef591a61
Source dataset
uspto-grants-2000_12
Patent number
US06162819

Reaction notes

Loading…