Methanol → HCID 58087146, compound

HRID 250585Notes

Reaction equation

HRID 250585 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-d2a2403d3ac243cfa068b24be126ccc2
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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