Hydrochloric Acid → 3-(4-Fluorophenyl)-5-(2-Phenylethynyl)-1H-Indazole

HRID 2183143Notes

Reaction equation

HRID 2183143 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[C:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:15]=3)[N:10](C3CCCCO3)[N:9]=2)=[CH:4][CH:3]=1.Cl>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[C:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:15]=3)[NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 224802083-(4-fluorophenyl)-5-(2-phenylethynyl)-1-(tetrahydropyran-2-yl)-1H-indazole

Product 1

HCID 224801623-(4-Fluorophenyl)-5-(2-Phenylethynyl)-1H-IndazoleYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(4-fluorophenyl)-5-(2-phenylethynyl)-1-(tetrahydropyran-2-yl)-1H-indazole in tetrahydrofuran (15 mL) was added 6 N hydrochloride solution (10 mL) and the mixture was stirred at ambient temperature overnight. After tetrahydrofuran was evaporated, the aqueous phase was neutralized with 5% sodium carbonate and extracted with ethyl acetate. The extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was then purified by chromatography (SiO2, 15-30% ethyl acetate/hexane) to provide the title compound (0.071 g, 90% yield). 1H NMR (CDCl3) δ 10.19 (br, 1H), 8.20 (s, 1H), 7.94-7.98 (m, 2H), 7.55-7.61 (m, 3H), 7.48 (dd, 1H), 7.34-7.41 (m, 3H), 7.23 (t, 2H); ES-MS (m/z) 313 [M+1]+.

Workup

  1. customAfter tetrahydrofuran was evaporated
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was then purified by chromatography (SiO2, 15-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d23eca6baec649f794ea41cd719d4300
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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