Methanol → HCID 16045079, compound

HRID 1012542Notes

Reaction equation

HRID 1012542 reaction equation
[F:1][C:2]1[C:3]([CH:22]=O)=[CH:4][N:5]([S:13]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)(=[O:15])=[O:14])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:24][NH2:25].[BH4-].[Na+].CO>O1CCCC1>[F:1][C:2]1[C:3]([CH2:22][NH:25][CH3:24])=[CH:4][N:5]([S:13]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)(=[O:15])=[O:14])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 866309754-fluoro-5-phenyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde

Product 1

HCID 16045079HCID 16045079, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Fluoro-5-phenyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (0.27 g) was dissolved in tetrahydrofuran (10 mL), a 2 mol/L solution (0.8 mL) of methylamine in tetrahydrofuran was added, and the mixture was stirred at room temperature for 2 hr. Sodium borohydride (91 mg) and methanol (7 mL) were added, and the mixture was stirred at the same temperature for further 30 min. The reaction mixture was concentrated under reduced pressure. A saturated aqueous sodium hydrogencarbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane-ethyl acetate=19:1→0:1). The above-mentioned operation was repeated to give the title compound (0.22 g, yield 39%) as a colorless solid.

Workup

  1. stirringthe mixture was stirred at the same temperature for further 30 min
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionA saturated aqueous sodium hydrogencarbonate solution was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe extract was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (hexane-ethyl acetate=19:1→0:1)

Sources & evidence

ORD record
ord-84f54f266a9442f38a7f7d9bd22d6390
Source dataset
uspto-grants-2011_07
Patent number
US07977488B2

Reaction notes

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