Water → HCID 86689213, compound

HRID 594944Notes

Reaction equation

HRID 594944 reaction equation
[C:1]([N:5]1[C:13]2[CH2:12][CH2:11][CH:10]([C:14]([O:16][CH3:17])=[O:15])[CH2:9][C:8]=2[C:7]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[Li+].[CH3:25]C([N-]C(C)C)C.CI.O>C1COCC1>[C:1]([N:5]1[C:13]2[CH2:12][CH2:11][C:10]([CH3:25])([C:14]([O:16][CH3:17])=[O:15])[CH2:9][C:8]=2[C:7]([C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 66804019HCID 66804019, compound

Product 1

HCID 86689213HCID 86689213, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-25 °C

Procedure

To methyl 1-tert-butyl-3-(pyridin-4-yl)-4,5,6,7-tetrahydro-1H-indazole-5-carboxylate (1.6 g, 5 mmol) in dry THF (20 mL) at −78° C. was added LDA (2 M, 5.5 mmol). The reaction temperature was increase to −25° C. for 1 h and was then cooled down to −78° C., MeI (16 mmol) was added and stood at r.t. for overnight, 20 ml water was added, most of the solvent was removed by distillation and the product was extracted with ethyl acetate, purified using silica chromatography (ethyl acetate/hexane) to give the desired product as yellow solid (1.1 g). LC-MS found 328.2 (M+H)

Workup

  1. temperaturewas then cooled down to −78° C.
  2. customwas removed by distillation
  3. extractionthe product was extracted with ethyl acetate
  4. custompurified

Sources & evidence

ORD record
ord-6409cd0f072d4af6be651eab01d617d1
Source dataset
uspto-grants-2016_01
Patent number
US09242981B2

Reaction notes

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