Triethylamine → HCID 58172051, compound
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][CH2:17][C:18](O)=[O:19])=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:5])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[N-:35]=[N+:36]=[N-:37].[Na+]>CC(C)=O.O>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][CH2:17][C:18]([N:35]=[N+:36]=[N-:37])=[O:19])=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:5])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -5 °C
Procedure
5-Bromo-3-(3-carboxy-propyl)-1H-indole-2-carboxylic acid ethyl ester (1.2 g, 3.40 mmol, 1.0 equiv) (see Example 2) was dissolved in 30 mL of acetone, cooled to −5° C. and triethylamine (0.76 ml, 5.44 mmol, 1.6 equiv) was added. To this cold solution, ethyl chloroformate (0.6 mL, 5.44 mmol, 1.6 equiv) was added dropwise and the mixture was stirred for 30 min at 0° C. A solution of sodium azide (440 mg, 6.8 mmol, 2.0 equiv) in 2 mL of water was added slowly and the mixture was stirred for a further 1 h at 0° C. The reaction mixture was then poured into ice-water (50 mL) and extracted 3×50 mL of diethyl ether. The pooled organic fractions were washed with 1×50 mL of water, 1×50 mL of saturated sodium bicarbonate, 1×50 mL of water, dried (Na2SO4), filtered and evaporated on the rotovap to provide 3-(3-azidocarbonyl-propyl)-5-bromo-1H-indole-2-carboxylic acid ethyl ester (1.28 g, 100%) which was used without further purification.
Workup
- stirringthe mixture was stirred for a further 1 h at 0° C
- extractionextracted 3×50 mL of diethyl ether
- washThe pooled organic fractions were washed with 1×50 mL of water, 1×50 mL of saturated sodium bicarbonate, 1×50 mL of water
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customevaporated on the rotovap
Sources & evidence
- ORD record
- ord-0404499dd5fa4581832e5e6a8b6bc860
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063094B2
Reaction notes
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