Imidazole → 6-Benzyloxy-1-[2-(tert-butyldimethyl-silanyloxy)-propyl]-1H-indazole

HRID 1815951Notes

Reaction equation

HRID 1815951 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[N:14][N:15]2[CH2:18][CH:19]([OH:21])[CH3:20])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[C:27]([Si:31](Cl)([CH3:33])[CH3:32])([CH3:30])([CH3:29])[CH3:28].C([O-])(=O)C.[NH4+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[N:14][N:15]2[CH2:18][CH:19]([O:21][Si:31]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:33])[CH3:32])[CH3:20])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 517165Ammonium AcetateHCID 9878877HCID 9878877, compound

Product 1

HCID 224965766-Benzyloxy-1-[2-(tert-butyldimethyl-silanyloxy)-propyl]-1H-indazoleYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-(6-benzyloxyindazol-1-yl)-propan-2-ol (10 g, 35.5 mmol) in THF (100 mL) and imidazole (3.4 g, 50 mmol) was added tert-butyl-chloro-dimethyl-silane (6.42 g, 42.6 mmol) and the mixture was stirred for 15 min at ambient temperature. The reaction mixture was poured into a saturated aqueous solution of ammonium acetate (300 mL) and extracted with ethyl acetate (2×150 mL). Purification by chromatography (silica, EtOAc/hexane) gave a yellow solid (10.6 g, 76%): mp 56-58° C.; LC/MS (+APCI) m/z 397 (M+H).

Workup

  1. extractionextracted with ethyl acetate (2×150 mL)
  2. customPurification by chromatography (silica, EtOAc/hexane)

Sources & evidence

ORD record
ord-74fd160ecf0148179a131e9a08ca859d
Source dataset
uspto-grants-2005_04
Patent number
US06881749B2

Reaction notes

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