Hydrochloric Acid → HCID 59370708, compound

HRID 1873957Notes

Reaction equation

HRID 1873957 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:24]=[O:25])=[N:14][N:15]2[CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][Mg]Br.C1COCC1.Cl>C1COCC1>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:24]([OH:25])[CH3:26])=[N:14][N:15]2[CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 59370712HCID 59370712, compoundHCID 178420675HCID 178420675, compound2×

Product 1

HCID 59370708HCID 59370708, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(6-(Benzyloxy)-1-(tetrahydro-2H-pyran-2-yl)-indazole-3-carbaldehyde (16.7 mg) which can be prepared according to the method described in Reference example 23, etc. was dissolved in dehydrated THF (0.5 mL; manufactured by Kanto Chemical Co., Inc.). After cooling to 0° C. with the replacement with nitrogen, 0.96 mol/L-methylmagnesium bromide-THF solution (57 μL; manufactured by Kanto Chemical Co., Inc.) and the mixture was stirred overnight while warming to room temperature. To the reaction solution, dehydrated THF (1 mL; manufactured by Kanto Chemical Co., Inc.) and 0.96 mol/L-methylmagnesium bromide-THF solution (1 mL; manufactured by Kanto Chemical Co., Inc.) were added and the mixture was stirred at room temperature for 4.5 hours. To the reaction solution, 2 mol/L hydrochloric acid was added and extraction was carried out twice with ethyl acetate. The organic layer was washed twice with water and once with brine and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by column chromatography (“COLUMN-F”; n-hexane:ethyl acetate 2:1) to obtain the title compound (11.4 mg).

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at room temperature for 4.5 hours
  3. extractionextraction
  4. washThe organic layer was washed twice with water and once with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter the solvent was evaporated under reduced pressure
  7. customthe residue was purified by column chromatography (“COLUMN-F”; n-hexane:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-b6188faae35e4da3bf91355f26facba0
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

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