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2-Bromopropane → 5-iodo-1-isopropyl-1H-indazole

HRID 13159
Notes
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Reaction equation

HRID 13159 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[CH:11](Br)([CH3:13])[CH3:12].[CH3:15][C:16]([O-])(C)[CH3:17].[K+].C(OCC)(=O)C>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]([CH3:13])[CH3:12])[N:6]=[CH:5]2.[I:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH:16]([CH3:17])[CH3:15])[N:7]=2)[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 63582-BromopropaneHCID 8857Ethyl AcetateHCID 218947395-Iodo-1H-indazoleHCID 23665647Potassium tert-butoxide

Product 2

HCID 593398645-iodo-1-isopropyl-1H-indazoleYield 52%HCID 666878755-iodo-2-isopropyl-2H-indazoleYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-iodo-1H-indazole (488 mg, 2 mmol), isopropyl bromide (244 mg, 2 mmol), and KOtBu (336 mg, 3 mmol) in dry DMF (4 ml) was stirred at r.t. overnight. Then it was dilited with ethyl acetate (50 ml), washed with water (2×50 ml), and dried with Na2SO4. Evaporation of solvent and purification by flash chromatography on silica gel (n-heptane/ethyl acetate) afforded the subtitle compound (298 mg, 52%) along with 5-iodo-2-isopropyl-2H-indazole (227 mg, 40%).

Workup

  1. washwashed with water (2×50 ml)
  2. dry with materialdried with Na2SO4
  3. customEvaporation of solvent and purification by flash chromatography on silica gel (n-heptane/ethyl acetate)

Sources & evidence

ORD record
ord-5a3fa000bf054b129bf75e466204c84d
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728030B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes