Methanol → HCID 66678389, compound

HRID 1261164Notes

Reaction equation

HRID 1261164 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-ece9017a8f164a7597cc97f1e0daf082
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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