Methanol → HCID 58087146, compound

HRID 1261041Notes

Reaction equation

HRID 1261041 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[Cl:10][C:11]1[CH:28]=[CH:27][C:14]([CH2:15][O:16][C:17]2[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][C:18]=2[O:25][CH3:26])=[CH:13][CH:12]=1.[CH3:29]O.[OH-].[K+]>C(OCC)(=O)C.O>[Cl:10][C:11]1[CH:28]=[CH:27][C:14]([CH2:15][O:16][C:17]2[CH:24]=[CH:23][C:20]([CH:21]([O:22][CH3:29])[C:3]3[C:4]4[C:9](=[N:8][CH:7]=[CH:6][CH:5]=4)[NH:1][CH:2]=3)=[CH:19][C:18]=2[O:25][CH3:26])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14797Potassium HydroxideHCID 7182634-[(4-Chlorophenyl)methoxy]-3-methoxybenzaldehyde

Product 1

HCID 58087146HCID 58087146, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1H-Pyrrolo[2,3-b]pyridine (94, 0.235 g, 1.99 mmol) and 4-(4-chlorobenzyloxy)-3-methoxybenzaldehyde (106, 0.500 g, 1.81 mmol) was added 5 mL of methanol followed by the addition of solid potassium hydroxide (0.203 g, 3.61 mmol). The reaction was allowed to stir at ambient temperature for 18 days. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was separated and volatiles removed to give a solid which was suspended in hot ethyl acetate. The suspension was allowed to cool and the solid collected by vacuum filtration to provide 107 (548 mg, 74%). MS (ESI) [M+H+]+=409.4.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. customvolatiles removed
  4. customto give a solid which
  5. temperatureto cool
  6. filtrationthe solid collected by vacuum filtration

Sources & evidence

ORD record
ord-da5a815c587d43c095171e2bcf851402
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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