Pyrrolidine → HCID 10200540, compound

HRID 966497Notes

Reaction equation

HRID 966497 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][CH2:22][CH2:23]Br)[CH:18]=2)[NH:13][C:12]=1[CH3:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>C(#N)C>[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][CH2:22][CH2:23][N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[CH:18]=2)[NH:13][C:12]=1[CH3:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 23393877HCID 23393877, compound

Product 1

HCID 10200540HCID 10200540, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-(3-Bromo-propoxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (0.244 g, 0.605 mmol, 1 eq) was suspended in dry acetonitrile (10 mL) under Ar. Pyrrolidine (0.100 mL, 1.210 mmol, 2 eq) was added. The reaction mixture was stirred and heated to reflux for 24 hours. Then the reaction was quenched with saturated sodium bicarbonate and extracted with ethyl acetate (3×). The combined organic phases were washed with brine and dried over Na2SO4. After removing the solvent, the residue was loaded on silica gel and chromatographed, eluting with ethyl acetate/methanol/triethyl amine (100/10/1). 0.100 g (42%) of the indole-pyrrolidine was obtained as a white solid. This was converted to the .HCl salt. LC/MS (ESI+) 393 (M+1); Anal. Calcd for C24H28N2O3.HCl.H2O: C, 64.49; H, 6.99; N, 6.27; Found: C, 64.36; H, 6.93; N, 6.15.

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hours
  3. customThen the reaction was quenched with saturated sodium bicarbonate
  4. extractionextracted with ethyl acetate (3×)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over Na2SO4
  7. customAfter removing the solvent
  8. customchromatographed
  9. washeluting with ethyl acetate/methanol/triethyl amine (100/10/1)

Sources & evidence

ORD record
ord-990ad84b20f743418a3cf26ed248e8c8
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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