Dimethylacetamide → 1-benzyl-3-chloro-7-cyano-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 642431
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:24])=[C:8]2[C:15]([Cl:16])=[CH:14][N:13]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:9]2=[C:10](Cl)[N:11]=1)=[O:5])[CH3:2].C[C:26]([N:28](C)C)=O>[C-]#N.[C-]#N.[Zn+2].[Zn].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:24])=[C:8]2[C:15]([Cl:16])=[CH:14][N:13]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:9]2=[C:10]([C:26]#[N:28])[N:11]=1)=[O:5])[CH3:2]

Komponenten

7

Edukt 2

HCID 31374DimethylacetamideHCID 866173511-Benzyl-3,7-dichloro-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Produkt 1

HCID 684284231-benzyl-3-chloro-7-cyano-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 23994ZincKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 1-benzyl-3,7-dichloro-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (155 mg), Zn(CN)2 (30 mg), Zn dust (3.3 mg), Pd2(dba)3 (19.4 mg), dppf (23.5 mg) in DMA (1.5 mL) was heated to 120° C. for 90 min; then the mixture was partitioned between EtOAc and water, the organic phase was then washed with sat. NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated sequentially to give a residue, which was purified with column to give desired title compound (100 mg). 1H NMR (200 MHz, CDCl3): δ(ppm)=12.16 (s, 1H), 7.4-7.1 (m, 6H), 5.71 (s, 2H), 4.53 (q, 2H, J=7.1 Hz), 1.49 (t, 3H, J=7.1 Hz).

Aufarbeitung

  1. customthen the mixture was partitioned between EtOAc and water
  2. washthe organic phase was then washed with sat. NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated sequentially
  6. customto give a residue, which
  7. customwas purified with column

Quellen und Nachweise

ORD-Eintrag
ord-6d90022b6a224118a7bb782d379bd551
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696223B2

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