(3-(Benzyloxy)phenyl)hydrazine hydrochloride → HCID 178437986, compound

HRID 2240170Notes

Reaction equation

HRID 2240170 reaction equation
C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH2:24][CH3:25])=[N:12][N:13]2COCC[Si](C)(C)C)=[CH:9][CH:8]=1)=O.Cl.[CH2:28]([O:35][C:36]1[CH:37]=[C:38]([NH:42]N)[CH:39]=[CH:40][CH:41]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(O)C>[CH2:28]([O:35][C:36]1[CH:37]=[C:38]([N:42]2[C:5]([C:7]3[CH:15]=[C:14]4[C:10]([C:11]([CH2:24][CH3:25])=[N:12][NH:13]4)=[CH:9][CH:8]=3)=[CH:4][CH:3]=[N:2]2)[CH:39]=[CH:40][CH:41]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 12891839(3-(Benzyloxy)phenyl)hydrazine hydrochlorideHCID 59810801HCID 59810801, compound

Product 1

HCID 178437986HCID 178437986, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2E)-3-(dimethylamino)-1-(3-Ethyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazol-6-yl)prop-2-en-1-one (256 mg, 0.685 mmol) and 3-benzyloxyphenylhydrazine hydrochloride (270 mg, 1.1 mmol) were dissolved in ethanol (4 mL) in a 10 mL sealed tube. The mixture was subjected to microwave radiation (300 watts, 160° C.) for 5 minutes. The solvent was removed and the residue was extracted with ethyl acetate, then washed with water and brine. Removal of volatiles provided a tan solid, which was purified by column chromatography on silica gel, eluting with a 10-50% hexane/ethyl acetate gradient over 10 minutes (flow rate 20 mL/min), to give 160 mg (59%) of 6-{1-[3-(benzyloxy)phenyl]-1H-pyrazol-5-yl}-3-ethyl-1H-indazole. 1 H NMR (CDCl3) δ 1.4 (t, 3H), 3.0 (q, 2H), 5.0 (s, 2H), 6.6 (d, 1H), 6.8 (d, 1H), 6.9 (d, 1H), 7.1 (m, 2H), 7.2 (t, 1H), 7.3, (m, 5H), 7.6 (d, 1H), 7.8 (m, 1H), 9.7 (br s, 1H).

Workup

  1. customsealed tube
  2. customThe solvent was removed
  3. extractionthe residue was extracted with ethyl acetate
  4. washwashed with water and brine
  5. customRemoval of volatiles
  6. customprovided a tan solid, which
  7. customwas purified by column chromatography on silica gel
  8. washeluting with a 10-50% hexane/ethyl acetate gradient over 10 minutes (flow rate 20 mL/min)

Sources & evidence

ORD record
ord-48deaabea6b84062933a7016c0bd5adf
Source dataset
uspto-grants-2010_05
Patent number
US07723348B2

Reaction notes

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