Sodium hydride → HCID 15906049, compound

HRID 1458628Notes

Reaction equation

HRID 1458628 reaction equation
Cl[C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[H-].[Na+].Br[CH2:18][CH2:19][CH2:20][NH2:21]>C1COCC1.C1(C)C=CC=CC=1>[NH:21]1[C:2]2=[C:10]([C:11]([O:13][CH3:14])=[O:12])[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]2[CH2:18][CH2:19][CH2:20]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 787023-BromopropylamineHCID 19599424Methyl 2-chloro-1H-indole-3-carboxylate

Product 1

HCID 15906049HCID 15906049, compoundYield 6.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 2-chloroindole-3-carboxylate (D11a, 1.5 g, 0.0071 mole) in THF (30 ml) under argon was treated with sodium hydride (215 mg of 80% oil dispersion, 0.0071 mole) and stirred for 20 minutes. The resulting solution was treated with a solution of 3-bromopropylamine (0.0093 mole) in toluene (15 ml) and a white gelatinous precipitate formed. This mixture was diluted with more THF (30 ml) and heated under reflux for 18 h, then concentrated in vacuo and the residue shaken well with ethyl acetate (40 ml) and 10% Na2CO3 solution (30 ml). The organic layer was separated, dried (Na2SO4) and concentrated in vacuo to leave a beige solid. This was chromatographed on silica gel eluting with ether/60-80 petrol (1:1) to afford unreacted starting material (600 mg) and the title compound (D 18) as a white solid (110 mg, 6%).

Workup

  1. customa white gelatinous precipitate formed
  2. temperatureheated
  3. temperatureunder reflux for 18 h
  4. concentrationconcentrated in vacuo
  5. stirringthe residue shaken well with ethyl acetate (40 ml) and 10% Na2CO3 solution (30 ml)
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customto leave a beige solid
  10. customThis was chromatographed on silica gel eluting with ether/60-80 petrol (1:1)
  11. customto afford unreacted

Sources & evidence

ORD record
ord-947de0a97c3e4a618f95680d14ebefc5
Source dataset
uspto-grants-1998_12
Patent number
US05852014

Reaction notes

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