Methanol → HCID 66678389, compound

HRID 1098524Notes

Reaction equation

HRID 1098524 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][C:13]=1[O:20][CH2:21][C:22]([F:25])([F:24])[F:23].[OH-:26].[K+].O.[CH3:29]O>>[CH3:29][O:26][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:1]([CH3:2])[C:16]=1[C:15]1[CH:18]=[CH:19][C:12]([O:11][CH3:10])=[C:13]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])[CH:14]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 962WaterHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14797Potassium HydroxideHCID 126475004-Methoxy-3-(2,2,2-trifluoroethoxy)benzaldehyde

Product 1

HCID 66678389HCID 66678389, compound

Conditions

Temperature
50 °C

Procedure

1H-Pyrrolo[2,3-b]pyridine (0.2 g, 1.8 mmol), 4-methoxy-3-(2,2,2-trifluoro-ethoxy)-benzaldehyde (562, 0.4 g, 1.9 mmol) and potassium hydroxide (0.5 g, 9.6 mmol) were combined in methanol (20 mL). The reaction was heated to 50° C. under an atmosphere of nitrogen and stirred for two days. The reaction was poured into water, extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The compound was isolated by silica gel column chromatography eluting with 40% to 75% ethyl acetate in hexanes to give orange oil (563, 0.2 g, 31%). MS (ESI) [M+H+]+=367.2 [M−H+]−=365.1.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe compound was isolated by silica gel column chromatography
  7. washeluting with 40% to 75% ethyl acetate in hexanes
  8. customto give orange oil (563, 0.2 g, 31%)

Sources & evidence

ORD record
ord-f9d2e25d85a74a908ff0fa9d4f4177eb
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

Loading…