Triethylamine → HCID 66925255, compound

HRID 554448Notes

Reaction equation

HRID 554448 reaction equation
[C:1]1([C:7]2[N:11]([S:12]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)(=[O:14])=[O:13])[CH:10]=[C:9]([CH:21]=O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:23]([N:25](CC)[CH2:26]C)C.[ClH:30].CNC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(OCC)(=O)C>[ClH:30].[ClH:30].[CH3:23][N:25]([CH3:26])[CH2:21][C:9]1[CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:11]([S:12]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)(=[O:14])=[O:13])[CH:10]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 862328815-phenyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde

Product 1

HCID 66925255HCID 66925255, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Phenyl-1-(3-pyridinesulfonyl)-1H-pyrrole-3-carbaldehyde (230 mg) was dissolved in dichloromethane (20 mL), triethylamine (0.52 mL), dimethylamine hydrochloride (302 mg), sodium triacetoxyborohydride (1.06 g) were added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed successively with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate-methanol=1:0→1:1) to give a free base of the title compound. The obtained free base was dissolved in ethyl acetate (3 mL), a 4 mol/L hydrogen chloride-ethyl acetate solution (1 ml) and ethanol (2 mL) were added, and the mixture was concentrated under reduced pressure. The residue was crystallized from ethanol to give the title compound (yield 138 mg, 45%).

Workup

  1. washwashed successively with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate-methanol=1:0→1:1)

Sources & evidence

ORD record
ord-51b2fb8c5ffc43559a8c60b295984c72
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

Loading…