Chloroform → HCID 53987743, compound

HRID 1722143Notes

Reaction equation

HRID 1722143 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.[C:17](=[O:20])([OH:19])[O-].[Na+].Cl[CH:23](Cl)Cl.Cl[C:27]([O:29][CH3:30])=[O:28]>O.O1CCCC1>[CH3:23][O:19][C:17]([N:14]1[CH2:15][CH2:16][CH:11]([C:6]2[C:5]3[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:8]([C:27]([O:29][CH3:30])=[O:28])[N:7]=2)[CH2:12][CH2:13]1)=[O:20]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 178477868HCID 178477868, compound

Product 1

HCID 53987743HCID 53987743, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 5.8 g of 6-chloro-3-(4-piperidinyl)-1H-indazole, 4.6 g of sodium bicarbonate and trichloromethane (25 ml)-tetrahydrofuran (25 ml) was added, dropwise, 5.2 g of methyl chloroformate. The reaction mixture was stirred at ambient temperature for 16 hrs and then poured into water. The organic layer was collected, washed with water, dried over anhydrous potassium carbonate and the solvent concentrated to give 4-(6-chloro-1-methyoxycarbonyl-1H-indazol-3-yl)piperidine-1-carboxylic acid methyl ester, as an oil. The oil was dissolved in 50 ml of methanol and 1.5 ml of a 25% sodium methoxide-methanol solution was added. The reaction mixture was stirred at ambient temperature for 0.5 hrs, poured into water and the aqueous mixture extracted with dichloromethane. The dichloromethane extract was washed with water, dried over anhydrous magnesium sulfate and the solvent evaporated to an oil. The oil was triturated with hexane. Recrystallization from toluene-hexane (twice) yielded 3.5 g (47%) of product, mp 132°-134° C.

Workup

  1. additionwas added
  2. customThe organic layer was collected
  3. washwashed with water
  4. dry with materialdried over anhydrous potassium carbonate
  5. concentrationthe solvent concentrated

Sources & evidence

ORD record
ord-6d0027d99ca648248d19c26c1a922eab
Source dataset
uspto-grants-1989_08
Patent number
US04853470

Reaction notes

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