Water → HCID 22661453, compound

HRID 393012Notes

Reaction equation

HRID 393012 reaction equation
Br[CH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[N:6][N:7]2[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1.[N-:18]=[N+:19]=[N-:20].[Na+].O>CN(C)C=O>[N:18]([CH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[N:6][N:7]2[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)=[N+:19]=[N-:20]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 226612154-Bromomethyl-1-(tetrahydro-pyran-2-yl)-1H-indazole

Product 1

HCID 22661453HCID 22661453, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-bromomethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (150 mg, 0.508 mmol) and sodium azide (132 mg, 2.0 mmol) in N,N-dimethylformamide (1.5 mL) was heated in a 90° C.-oil-bath for 30 min, then allowed to cool, and poured into water (5 mL). The mixture was extracted with ether (2×10 mL), dried (MgSO4), filtered, evaporated, and dried under high vacuum overnight to give 4-azidomethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (124 mg, 95%) as a yellow oil.

Workup

  1. temperatureto cool
  2. extractionThe mixture was extracted with ether (2×10 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-a5ba32112ad645ca9e7e2450d9bb204c
Source dataset
uspto-grants-2004_10
Patent number
US06803384B2

Reaction notes

Loading…