Sodium hydride → 1-(2-propynyl)-2-trifluoromethyl-(1H)-indole

HRID 231837

Reaction equation

HRID 231837 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[H-].[Na+].Br[C:17]#[C:18][CH3:19].P(O)(O)([O-])=O.[Na+]>O1CCCC1>[CH2:19]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[C:3]1[C:2]([F:1])([F:12])[F:13])[C:18]#[CH:17]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 1372791-Propyne, 1-bromo-HCID 109321242-(trifluoromethyl)-1H-indoleHCID 23672064Monosodium phosphate

Product 1

HCID 178825791-(2-propynyl)-2-trifluoromethyl-(1H)-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8.57 g of 2-trifluoromethyl-1H-indole described in J. Org. Chem. (1983) 48-3233 and 10 ml of tetrahydrofuran were mixed together under an inert atmosphere at +5° C. and after 15 minutes, 2.4 g of sodium hydride in oil were added. After 2 minutes, 4.5 ml of 2-bromo-propyne were introduced and the resulting mixture was stirred for 30 minutes at +5° C., then for one hour at 25° C. Another 4.5 ml of bromo-propyne were added and the mixture was stirred for 4 hours and then poured into an iced solution of monosodium phosphate and extracted with ethyl ether. The extracts were concentrated to dryness by distillation under reduced pressure and the residue was chromatographed over silica and eluted with a mixture of hexane and ethyl acetate (95/5) to obtain 8.88 g of 1-(2-propynyl)-2-trifluoromethyl-(1H)-indole melting at 59° C.

Workup

  1. waitfor one hour at 25° C
  2. stirringthe mixture was stirred for 4 hours
  3. extractionextracted with ethyl ether
  4. concentrationThe extracts were concentrated to dryness by distillation under reduced pressure
  5. customthe residue was chromatographed over silica
  6. washeluted with a mixture of hexane and ethyl acetate (95/5)

Sources & evidence

ORD record
ord-0d5157f6691f44bab370f6cb3a62591d
Source dataset
uspto-grants-1989_07
Patent number
US04849443

Linked notes

Loading…