Propargyl bromide → HCID 12244397, compound

HRID 240773Notes

Reaction equation

HRID 240773 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[H-].[Na+].[CH2:12](Br)[C:13]#[CH:14]>CN(C)C=O.C(OCC)(=O)C>[CH2:14]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1)[C:13]#[CH:12]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 92211H-IndazoleHCID 24758Sodium hydride

Product 1

HCID 12244397HCID 12244397, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Indazole (530 mg, 4.49 mmol) was dissolved in dimethylformamide (4 mL). Sodium hydride (60% suspension in mineral oil, 231 mg, 5.78 mmol) was added slowly, and the mixture was stirred for 10 minutes. Propargyl bromide (80% wt in toluene, 5.0 mL) was added, and the mixture was stirred at ambient temperature overnight. The mixture was diluted with ethyl acetate, washed excessively with water, absorbed on silica gel, and purified by silica gel chromatography eluting with a gradient of 5-30% ethyl acetate in hexanes to afford the title compound. MS (ESI+) m/z 157.1 (M+H)+.

Workup

  1. stirringthe mixture was stirred at ambient temperature overnight
  2. washwashed excessively with water
  3. customabsorbed on silica gel
  4. custompurified by silica gel chromatography
  5. washeluting with a gradient of 5-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e8d61121ad4a45c3ba27417c231c3c1c
Source dataset
uspto-grants-2014_02
Patent number
US08648069B2

Reaction notes

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