sodium (1Z)-1-cyanoprop-1-en-2-olate → (2E)-2-[(6-fluoro-1H-indazol-5-yl)methylidene]-3-oxobutanenitrile

HRID 237409Notes

Reaction equation

HRID 237409 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[CH:11]=O.[C:13](/[CH:15]=[C:16](\[O-:18])/[CH3:17])#[N:14].[Na+]>>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1/[CH:11]=[C:15](/[C:16](=[O:18])[CH3:17])\[C:13]#[N:14]

Participants

3

Reactant 2

HCID 23687916sodium (1Z)-1-cyanoprop-1-en-2-olateHCID 579172916-fluoro-1H-indazole-5-carbaldehyde

Product 1

HCID 66616240(2E)-2-[(6-fluoro-1H-indazol-5-yl)methylidene]-3-oxobutanenitrile

Procedure

The title compound was prepared from 3.7 g (80% purity, 18.0 mmol) 6-fluoro-1H-indazole-5-carbaldehyde (Example 13A) and 2.08 g (19.84 mmol) sodium (1Z)-1-cyanoprop-1-en-2-olate in analogy to the procedure described in Example 9A yielding 2.5 g (61% of th.) of product which was used in subsequent steps without further purification.

Workup

  1. customyielding 2.5 g (61% of th.) of product which
  2. customwas used in subsequent steps without further purification

Sources & evidence

ORD record
ord-6c26457a7e974c2a81b4c09bba72e7cd
Source dataset
uspto-grants-2014_02
Patent number
US08642595B2

Reaction notes

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