Imidazole → HCID 59370713, compound

HRID 1671279Notes

Reaction equation

HRID 1671279 reaction equation
N1C=CN=C1.[C:6]([Si:10](Cl)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:9])([CH3:8])[CH3:7].[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([OH:33])[CH:31]=2)[CH:26]=[N:25]1.O>CN(C)C=O>[O:33]([C:30]1[CH:31]=[C:32]2[C:27]([CH:26]=[N:25][NH:24]2)=[CH:28][CH:29]=1)[Si:10]([C:6]([CH3:9])([CH3:8])[CH3:7])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 1354839876-hydroxy-1H-indazole

Product 1

HCID 59370713HCID 59370713, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (3.0 g, manufactured by Kanto Chemical Co., Inc.) and t-butylchlorodiphenylsilane (12.1 g, manufactured by Tokyo Chemical Industry Co., Ltd.) were added to a solution of 1H-indazol-6-ol (3.0 g) synthesized according to the literature (L. F. Fieser, J. Am. Chem. Soc., 1926, 48, 1097-1107) in N,N-dimethylformamide (100 mL, manufactured by Kanto Chemical Co., Inc.), and the mixture was stirred for 3 hours at room temperature. Water (200 mL) was added to the reaction solution, and the mixture was extracted with diethyl ether (3×200 mL), washed with brine (400 mL), and dried (MgSO4). The solvent was then evaporated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1), to give 7.3 g of the title compound. LC-MS: HPLC retention time 2.05 minutes, m/z 373 (M+H), condition C-1.

Workup

  1. customsynthesized
  2. extractionthe mixture was extracted with diethyl ether (3×200 mL)
  3. washwashed with brine (400 mL)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was then evaporated
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-fb9060dc590149cfaa29d9ef54435c6e
Source dataset
uspto-grants-2011_08
Patent number
US07994202B2

Reaction notes

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