Triethylamine → HCID 21922598, compound

HRID 1244999Notes

Reaction equation

HRID 1244999 reaction equation
C1(C)C=CC(S([O:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])(=O)=O)=CC=1.C(N(CC)CC)C.[F:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:40]=[CH:39][N:38]([CH2:41][CH2:42][CH2:43]O)[C:37]=2[C:45]2[CH:50]=[CH:49][N:48]=[CH:47][CH:46]=2)=[CH:32][CH:31]=1>ClCCl>[F:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:40]=[CH:39][N:38]([CH2:41][CH2:42][CH2:43][O:10][S:11]([C:14]3[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=3)(=[O:12])=[O:13])[C:37]=2[C:45]2[CH:46]=[CH:47][N:48]=[CH:49][CH:50]=2)=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77773Toluene-p-sulphonic anhydrideHCID 21922792HCID 21922792, compound

Product 1

HCID 21922598HCID 21922598, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.99 g (6.09 mmol) of p-toluenesulfonic anhydride and 0.85 ml (6.09 mmol) of triethylamine were added to a solution of 1.64 g (5.53 mmol) of 3-(4-fluorophenyl)-1-(3-hydroxypropyl)-2-(pyridin-4-yl)-1H-pyrrole [prepared as described in step 22(ii) above] in 16 ml of dichloromethane. The resulting mixture was stirred at room temperature for 2 hours, after which the solvent was distilled off by evaporation under reduced pressure. The resulting residue was purified by chromatography on a silica gel column using a 1:1 by volume mixture of hexane and ethyl acetate as the eluant to afford 1.33 g (yield 53%) of the title compound as a yellow powder.

Workup

  1. distillationafter which the solvent was distilled off by evaporation under reduced pressure
  2. customThe resulting residue was purified by chromatography on a silica gel column
  3. additionby volume mixture of hexane and ethyl acetate as the eluant

Sources & evidence

ORD record
ord-4b3a2302b9eb47a1a44a2df5539c80fd
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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