Diisopropylethylamine → 2-(5-Chloro-1-isobutyl-indazol-7-yl)acetonitrile

HRID 2203178Notes

Reaction equation

HRID 2203178 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11]O)[CH:10]=1)[N:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[N:6]=[CH:5]2.C[CH2:18][N:19](C(C)C)C(C)C.CS(OS(C)(=O)=O)(=O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][C:18]#[N:19])[CH:10]=1)[N:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[N:6]=[CH:5]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 118251601(5-Chloro-1-isobutyl-1H-indazole-7-yl)-methanol

Product 1

HCID 1182516492-(5-Chloro-1-isobutyl-indazol-7-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 17 (1 g, 4.2 mmol), at room temperature and under nitrogen atmosphere, in dry dichloromethane (10 mL) were added DIPEA (0.8 mL, 4.62 mmol) and methane sulfonic anhydride. (0.8 g, 4.62 mmol) The resulting mixture was stirred for 2 h. Then, the reaction mixture was quenched with water and the mixture was extracted with more dichloromethane. The organic layer was separated, washed with Brine, dried (MgSO4), filtered and the solvent evaporated to give the desired product as yellow oil.

Workup

  1. customThen, the reaction mixture was quenched with water
  2. extractionthe mixture was extracted with more dichloromethane
  3. customThe organic layer was separated
  4. washwashed with Brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-7be3b221fdc040d19b85737e88ef271d
Source dataset
uspto-grants-2016_06
Patent number
US09365569B2

Reaction notes

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