Hydrochloric Acid → HCID 58086261, compound

HRID 253380Notes

Reaction equation

HRID 253380 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[CH:15]=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH:2]=1.[CH2:16]([O:23][C:24]1[C:25]([F:33])=[C:26]([C:29]([F:32])=[CH:30][CH:31]=1)[CH:27]=[O:28])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[K+].Cl>CO.O>[CH2:16]([O:23][C:24]1[C:25]([F:33])=[C:26]([CH:27]([C:15]2[C:9]3[C:10](=[N:11][CH:12]=[C:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[CH:8]=3)[NH:13][CH:14]=2)[OH:28])[C:29]([F:32])=[CH:30][CH:31]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 5613532,6-Difluoro-3-(phenylmethoxy)benzaldehydeHCID 513585515-(Pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 58086261HCID 58086261, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine (20, 750.0 mg, 0.003842 mol, prepared as in Example 9) in methanol (20.0 mL) were added 3-benzyloxy-2,6-difluoro-benzaldehyde (27, 1.12 g, 4.5 mmol) and potassium hydroxide (1.50 g, 0.0267 mol) under an atmosphere of nitrogen. The reaction was stirred at room temperature overnight and then poured into water, acidified with 1N HCl to pH around 2 and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give the compound (28, 700 mg, 35%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 20% ethyl acetate in hexane
  7. customto give the compound (28, 700 mg, 35%)

Sources & evidence

ORD record
ord-ca9ec0946be345a8a16dc15682d62b3a
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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