Potassium Hydroxide → 5-[(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-pyridin-2-yl-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester

HRID 1256811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256811
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[C:11]([O:15][C:16](=[O:35])[N:17]([C:27]1[CH:32]=[CH:31][C:30]([CH:33]=[O:34])=[CH:29][N:28]=1)[CH2:18][C:19]1[CH:20]=[N:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1)([CH3:14])([CH3:13])[CH3:12].COC1N=CC(C=O)=CC=1.[OH-].[K+]>CO.O>[C:11]([O:15][C:16](=[O:35])[N:17]([C:27]1[CH:32]=[CH:31][C:30]([CH:33]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[NH:8][CH:9]=2)[OH:34])=[CH:29][N:28]=1)[CH2:18][C:19]1[CH:20]=[N:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1)([CH3:14])([CH3:12])[CH3:13]

Komponenten

7

Edukt 4

HCID 14797Potassium HydroxideHCID 33645766-Methoxypyridine-3-carbaldehydeHCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 57619225(5-Formyl-pyridin-2-yl)-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester

Produkt 1

HCID 576194035-[(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-pyridin-2-yl-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl esterAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To 5-chloro-1H-pyrrolo[2,3-b]pyridine (532, 0.092 g, 0.60 mmol) in methanol (15.0 mL) were added (5-formyl-pyridin-2-yl)-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester (585, 0.240 g, 0.70 mmol, prepared according to the protocol of Example 17, Scheme 19, Steps 1-3, replacing 4-chlorobenzaldehyde 40 with 6-methoxy-pyridine-3-carbaldehyde in Step 1) and potassium hydroxide (1.2 g, 0.021 mol). The reaction was stirred at room temperature overnight, then poured into water, 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% to 100% ethyl acetate in hexane to give the desired compound (586, 0.110 g, 37%).

Aufarbeitung

  1. customprepared
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography
  7. washeluting with 20% to 100% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-35f8106ebe5e4586ba7c45511a1e12e9
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461169B2

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