Hydrochloric Acid → HCID 68669587, compound

HRID 1964917Notes

Reaction equation

HRID 1964917 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:12]=[C:13]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[CH:14]=[O:15].[OH-].[K+].Cl.[CH3:31]O>O>[Cl:10][C:11]1[CH:12]=[C:13]([CH2:14][O:15][C:3]2[C:4]3[C:9](=[N:8][CH:7]=[CH:6][CH:5]=3)[N:1]([CH3:31])[CH:2]=2)[CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14797Potassium HydroxideHCID 8187873-chloro-4-[(4-chlorobenzyl)oxy]benzaldehyde

Product 1

HCID 68669587HCID 68669587, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

1H-Pyrrolo[2,3-b]pyridine (94, 0.3 g, 2.8 mmol) was mixed with 3-chloro-4-(4-chloro-benzyloxy)-benzaldehyde (558, 0.8 g, 3 mmol), potassium hydroxide (0.9 g, 17 mmol) and methanol (90.0 mL). The reaction was heated to 50° C. under an atmosphere of nitrogen for six days. After neutralization with 6N hydrochloric acid 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 desired compound was isolated by silica gel column chromatography (ethyl acetate: hexanes) to give a yellow solid (559, 0.6 g, 41%). MS(ESI) [M+H+]+=413.2, 415.2 [M−H+]−=411.1, 413.1.

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

Sources & evidence

ORD record
ord-4fb63d9ac3ab4ccc9dea729e9b20ebf7
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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