Acetaldehyde → HCID 10112823, compound

HRID 857351Notes

Reaction equation

HRID 857351 reaction equation
Br[C:2]1[C:3]2[C:4]([S:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[C:5]3[CH:14]([CH2:15][C:16]([OH:18])=[O:17])[CH2:13][CH2:12][N:6]3[C:7]=2[CH:8]=[C:9]([F:11])[CH:10]=1.C[Mg+].[Br-].[Li]C(CC)C.[CH:35](=[O:37])[CH3:36]>C1COCC1>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([S:19][C:4]2[C:3]3[C:2]([CH:35]([OH:37])[CH3:36])=[CH:10][C:9]([F:11])=[CH:8][C:7]=3[N:6]3[CH2:12][CH2:13][CH:14]([CH2:15][C:16]([OH:18])=[O:17])[C:5]=23)=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 10226143HCID 10226143, compoundHCID 178418400CID 53628100HCID 178418689HCID 178418689, compound

Product 1

HCID 10112823HCID 10112823, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of (+/−)-[8-bromo-9-[(4-chlorophenyl)sulfanyl]-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl]acetic acid (Example 7, 100 mg, 0.22 mmol) in THF (4 mL) at −78° C. was added 3M MeMgBr (0.26 mmol) followed by the addition of 1.3M sec-BuLi (0.31 mmol). The reaction mixture was stirred at −78° C. for 5 minutes and an excess of acetaldehyde was added. The reaction was stirred at −78° C. for 30 minutes and quenched with saturated aqueous NH4Cl. The phases were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with EtOAc/Hexanes/AcOH (20:30:1) to provide 65 mg of the title compound as a white solid.

Workup

  1. stirringThe reaction was stirred at −78° C. for 30 minutes
  2. customquenched with saturated aqueous NH4Cl
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluted with EtOAc/Hexanes/AcOH (20:30:1)

Sources & evidence

ORD record
ord-1c0dae18d3954dc0b8e69bb0ecd61b4a
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

Loading…