Methyl propiolate → HCID 281151, compound

HRID 1095529Notes

Reaction equation

HRID 1095529 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1.[CH3:17][O:18][C:19](=[O:22])[C:20]#[CH:21]>CN(C)C(=O)C>[NH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([CH2:7][CH2:6][N:1]2[CH:21]=[C:20]([C:19]([O:18][CH3:17])=[O:22])[N:3]=[N:2]2)=[CH:9]1

Participants

5

Reactant 3

HCID 13536Methyl propiolateHCID 33557Sodium AzideHCID 769243-(2-Bromoethyl)indole

Product 1

HCID 281151HCID 281151, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

The resin (4-(bromomethyl)-phenoxyethyl-polystyrene HL) (5.00 g, 5.5 mmol) was suspended in N,N-dimethylacetamide (DMA) (30 ml), sodium azide (178 g, 27.5 mmol, 5 eq.) was added and the mixture was stirred at RT for 48 h. The resin was filtered off, washed with methanol and dried. The resin was suspended in DMA (100 ml) again, 3-(2-bromoethyl)indole (0.60 g, 2.67 mmol) was added and the mixture was stirred at RT for 5 d. Propiolic acid methyl ester (0.24 ml, 2.67 mmol) was then added, the mixture was stirred at 80° C. for 20 h and the solvent was removed i. vac. The residue was separated by flash chromatography with CHCl3/MeOH (9:1). In addition to the desired product, 3-(2-bromoethyl)indole (103 mg, 17%) was recovered. Yield: 342 mg (Ind-63, 47%)

Workup

  1. filtrationThe resin was filtered off
  2. washwashed with methanol
  3. customdried
  4. stirringthe mixture was stirred at RT for 5 d
  5. stirringthe mixture was stirred at 80° C. for 20 h
  6. customthe solvent was removed i
  7. customThe residue was separated by flash chromatography with CHCl3/MeOH (9:1)
  8. additionIn addition to the desired product, 3-(2-bromoethyl)indole (103 mg, 17%)
  9. customwas recovered

Sources & evidence

ORD record
ord-311192b77c1c42b586783ee5bfa60c9b
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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