Triethylamine → HCID 86691191, compound

HRID 709403Notes

Reaction equation

HRID 709403 reaction equation
ClC(OCC)=O.Cl.[Br:8][C:9]1[N:14]=[CH:13][C:12]([C@@H:15]2[CH2:17][C@H:16]2[C:18]([OH:20])=O)=[CH:11][CH:10]=1.CCN(CC)CC.[N-:28]=[N+:29]=[N-:30].[Na+]>CC(C)=O.O>[Br:8][C:9]1[N:14]=[CH:13][C:12]([C@@H:15]2[CH2:17][C@H:16]2[C:18]([N:28]=[N+:29]=[N-:30])=[O:20])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 86691192HCID 86691192, compound2×

Product 1

HCID 86691191HCID 86691191, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

Ethyl chloroformate (5.8 mL, 62 mmol) was added to a solution of (trans)-2-(6-bromopyridin-3-yl)cyclopropanecarboxylic acid hydrochloride (Intermediate E, 5 g, 20.7 mmol) and Et3N (14.2 mL, 103.7 mmol) in Acetone (100 mL) at −5° C., then reaction mixture was stirred at −5° C. for 1 h, then a solution of NaN3 (2.7 g, 41.4 mmol) in water (10 mL) was added and stirred for 30 mins at RT. After completion the solvent was evaporated under vacuum. The crude residue was dissolved in ethyl acetate (200 mL), washed with water (80 mL), brine (80 mL), dried over anhydrous Na2SO4, filtered and evaporated to get (trans)-2-(6-bromopyridin-3-yl)cyclopropanecarbonyl azide (2.5 g, 45.5%) as a brown color gummy liquid.

Workup

  1. customreaction mixture
  2. stirringstirred for 30 mins at RT
  3. customAfter completion the solvent was evaporated under vacuum
  4. dissolutionThe crude residue was dissolved in ethyl acetate (200 mL)
  5. washwashed with water (80 mL), brine (80 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-c508910f454243ddb19cbdbc447d145b
Source dataset
uspto-grants-2015_11
Patent number
US09181198B2

Reaction notes

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