Triethylamine → 1-(2-Chloropyridin-4-yl)carbonyl-1'-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3'-pyrrolidine]

HRID 83987

Reaction equation

HRID 83987 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([CH2:15]/[CH:16]=[CH:17]/[C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=4)[CH2:11]3)[CH2:9][NH:8][C:5]2=[CH:6][CH:7]=1.C(N(CC)CC)C.[Cl:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][N:41]=1)[C:36](Cl)=[O:37].C(=O)(O)[O-].[Na+]>ClCCl>[Cl:32][C:33]1[CH:34]=[C:35]([C:36]([N:8]2[C:5]3[C:4](=[CH:3][CH:2]=[CH:7][CH:6]=3)[C:10]3([CH2:14][CH2:13][N:12]([CH2:15]/[CH:16]=[CH:17]/[C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=4)[CH2:11]3)[CH2:9]2)=[O:37])[CH:39]=[CH:40][N:41]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 28000032-Chloropyridine-4-carbonyl chlorideHCID 689306495-Chloro-1'-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3'-pyrrolidine]

Product 1

HCID 866273631-(2-Chloropyridin-4-yl)carbonyl-1'-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3'-pyrrolidine]Yield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-chloro-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3′-pyrrolidine] (150 mg) and triethylamine (0.24 ml) in dichloromethane (5 ml) at 0° C. under argon was treated with 2-chloro-isonicotinoyl chloride (147 mg). The resulting solution was stirred at room temperature for 1 hour, poured into saturated aqueous sodium bicarbonate, extracted with ethyl acetate, dried (Na2SO4) and concentrated in vacuo. Silica gel chromatography of the residue (eluent cyclohexane:ethyl acetate 6:4) afforded the title compound, 1-(2-chloropyridin-4-yl)carbonyl-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3′-pyrrolidine] (95 mg), which was characterised by its mass and NMR spectra. MS (ES+) 498/500 (M+H+).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-274243220eae4859921604cb8134f577
Source dataset
uspto-grants-2014_09
Patent number
US08846907B2

Linked notes

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