Hydrochloric Acid → methyl 2-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)indole-6-carboxylate

HRID 2068877Notes

Reaction equation

HRID 2068877 reaction equation
C(OC([N:8]1[C:16]2[CH2:15][C:14]([CH3:18])([CH3:17])[CH2:13][CH2:12][C:11]=2[C:10]([C:19]2[N:20](C(OC(C)(C)C)=O)[C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[C:23]([C:28]([O:30][CH3:31])=[O:29])[CH:22]=3)=[N:9]1)=O)(C)(C)C.CO.[OH-].[Na+].Cl>O1CCCC1>[CH3:17][C:14]1([CH3:18])[CH2:15][C:16]2[NH:8][N:9]=[C:10]([C:19]3[NH:20][C:21]4[C:26]([CH:27]=3)=[CH:25][CH:24]=[C:23]([C:28]([O:30][CH3:31])=[O:29])[CH:22]=4)[C:11]=2[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 585501461-tert-butyl 6-methyl 2-(1-tert-butoxycarbonyl-6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)indole-1,6-dicarboxylate

Product 1

HCID 136127476methyl 2-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)indole-6-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-tert-butyl 6-methyl 2-(1-tert-butoxycarbonyl-6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)indole-1,6-dicarboxylate (39 g, 75 mmol) in a mixed solvent of methanol (180 ml) and tetrahydrofuran (120 ml) was added dropwise 2 N aqueous sodium hydroxide solution (149 ml, 298 mmol) under ice-cooling over 15 min, and the mixture was stirred for 15 min. Then, 1 N hydrochloric acid was added dropwise to adjust the pH to 5. The precipitated crystals were collected by filtration, washed with water, and dried under reduced pressure to give the title compound (23 g, yield 97%).

Workup

  1. temperaturecooling over 15 min
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-0bbc6eb4442448a58818a924b6e086df
Source dataset
uspto-grants-2012_10
Patent number
US08299070B2

Reaction notes

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