Benzyl Bromide → HCID 22663194, compound

HRID 380433Notes

Reaction equation

HRID 380433 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[NH:4][N:3]=1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O.O>[CH2:15]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:6]=2)[C:2]([CH3:1])=[N:3]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH2:15]([N:3]1[C:2]([CH3:1])=[C:10]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9]2)=[N:4]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 178497281HCID 178497281, compound

Product 2

HCID 22663194HCID 22663194, compoundHCID 22663327HCID 22663327, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of methyl 3-methyl-indazole-6-carboxylate (0.2 g, Reference Example 44) in acetone (15 ml) was treated with benzyl bromide (0.898 g) then with potassium carbonate (0.290 g) and a catalytic amount of 18-crown-6. The mixture was stirred for 12 hours at room temperature then poured into water (30 ml) and then extracted three times with ethyl acetate (30 ml). The combined extracts were dried over sodium sulphate then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and hexane (7:1, v/v) to yield the title compound (0.161 g) and methyl 2-benzyl-3-methyl-indazole-6-carboxylate (0.069 g).

Workup

  1. extractionextracted three times with ethyl acetate (30 ml)
  2. dry with materialThe combined extracts were dried over sodium sulphate
  3. customthen evaporated
  4. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and hexane (7:1

Sources & evidence

ORD record
ord-f68d4d002f6e4399bc015a9f1c6f749c
Source dataset
uspto-grants-2001_10
Patent number
US06303600B1

Reaction notes

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