Styrylboronic acid → 5-benzyloxy-3-((E)-styryl)-1H-indazole

HRID 1726049Notes

Reaction equation

HRID 1726049 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:15]=2)[C:10](I)=[N:9]1)=O)(C)(C)C.[C:26]1(/[CH:32]=[CH:33]/B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C)C=O.C(=O)(O)[O-].[Na+]>[CH2:18]([O:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:8][N:9]=[C:10]2/[CH:33]=[CH:32]/[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 5702628Styrylboronic acidHCID 575624111H-Indazole-1-carboxylic acid, 3-iodo-5-(phenylmethoxy)-, 1,1-dimethylethyl ester

Product 1

HCID 688442725-benzyloxy-3-((E)-styryl)-1H-indazoleYield 69%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The compound, 5-benzyloxy-3-((E)-styryl)-1H-indazole is prepared according to procedure C, step Ib, using 300 mg of 5-benzyloxy-3-iodoindazole-1-carboxylic acid tert-butyl ester, 197 mg of E-phenylethenyl boronic acid, 192 mg of palladium tetrakistriphenylphosphine in suspension in 12 ml of dimethylformamide and 0.61 ml of a saturated sodium bicarbonate solution. The resulting crude product is treated as described hereinabove to obtain 150 mg of 5-benzyloxy-3-((E)-styryl)-1H-indazole.

Workup

  1. customThe compound, 5-benzyloxy-3-((E)-styryl)-1H-indazole is prepared

Sources & evidence

ORD record
ord-b6ef7486c40e4589ae9e8b4b47b65414
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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