tert-Butyl bromoacetate → HCID 178451205, compound

HRID 343400Notes

Reaction equation

HRID 343400 reaction equation
Cl.[Br:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[N:8][NH:9]2)=[CH:5][CH:4]=1.Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH3:8].[C:23]([O:22][C:20](=[O:21])[CH2:19][N:15]1[CH2:16][CH2:17][CH:12]([C:7]2[C:6]3[C:10](=[CH:11][C:3]([Br:2])=[CH:4][CH:5]=3)[NH:9][N:8]=2)[CH2:13][CH2:14]1)([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 516892Sodium BicarbonateHCID 178419305HCID 178419305, compound

Product 2

HCID 222AmmoniaHCID 178451205HCID 178451205, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-bromo-3-piperidin-4-yl-1H-indazole hydrochloride (500 mg, 1.78 mmol), tert-butyl bromoacetate (0.29 ml, 1.78 mmol), sodium bicarbonate (150 mg, 1.87 mmol), and DMF (10 ml) was stirred at +23° under nitrogen for 18 h The mixture was evaporated in vacuo, treated with aqueous saturated sodium bicarbonate (25 ml), and extracted with ethyl acetate (50 ml). The dried (Na2SO4) organic layer was evaporated in vacuo onto silica gel (Merck 7734). Purification by flash chromatography over silica gel (Merck 9385), eluting with dichloromethane--ethanol--880 ammonia (gradient 967:30:3 to 945:50:5) afforded the title compound as fine white crystals (347 mg).

Workup

  1. customwas evaporated in vacuo
  2. additiontreated with aqueous saturated sodium bicarbonate (25 ml)
  3. extractionextracted with ethyl acetate (50 ml)
  4. dry with materialThe dried (Na2SO4) organic layer
  5. customwas evaporated in vacuo onto silica gel (Merck 7734)
  6. customPurification by flash chromatography over silica gel (Merck 9385)
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-c3aeedb40bc8494e84ca2351578a8e66
Source dataset
uspto-grants-1999_01
Patent number
US05861414

Reaction notes

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