Benzyl Bromide → HCID 22663194, compound

HRID 2054508Notes

Reaction equation

HRID 2054508 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-e0aab279fcd346e3b9c2abad0de5e5f7
Source dataset
uspto-grants-2008_02
Patent number
US07329675B2

Reaction notes

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