Sodium hydride → HCID 19599413, compound

HRID 1458624Notes

Reaction equation

HRID 1458624 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+].[CH3:17][NH:18][CH:19](NC)[CH2:20][CH2:21]Cl>C1COCC1.C1(C)C=CC=CC=1>[CH3:17][N:18]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[CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 19599424Methyl 2-chloro-1H-indole-3-carboxylateHCID 54275058HCID 54275058, compound

Product 1

HCID 19599413HCID 19599413, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-chloroindole-3-carboxylate (3.4 g, 0.016 mole) in dry THF (70 ml) at 5° C. under nitrogen was treated portionwise with sodium hydride (480 mg of 80% oil dispersion, 0.016 mole) and then stirred at room temperature for 30 mins. The resulting solution was treated with a solution of 3,3-dimethylaminopropyl chloride (0.020 mole) in toluene (30 ml) and heated under reflux for 48 h, then concentrated in vacuo and the residue treated with 10% Na2CO3 solution (50 ml) and extracted with ethyl acetate (2×70 ml). The combined extracts were dried (Na2SO4) and concentrated in vacuo to leave a yellow oil, which was chromatographed on silica gel eluting with ether/60-80 petrol (1:1). The title compound (D11) was obtained as a beige solid (1.95 g, 50%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 48 h
  3. concentrationconcentrated in vacuo
  4. additionthe residue treated with 10% Na2CO3 solution (50 ml)
  5. extractionextracted with ethyl acetate (2×70 ml)
  6. dry with materialThe combined extracts were dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customto leave a yellow oil, which
  9. customwas chromatographed on silica gel eluting with ether/60-80 petrol (1:1)

Sources & evidence

ORD record
ord-d859fe694121457d968aa40dadb80118
Source dataset
uspto-grants-1998_12
Patent number
US05852014

Reaction notes

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