Acetic Anhydride → (E)-1-acetyl-3-(2-(pyridin-4-yl)vinyl)-1H-indazole-6-carbonitrile

HRID 447515Notes

Reaction equation

HRID 447515 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[NH:5][N:4]=1)=O.[N:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>>[C:21]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([C:12]#[N:13])[CH:7]=2)[C:3](/[CH:1]=[CH:20]/[C:17]2[CH:18]=[CH:19][N:14]=[CH:15][CH:16]=2)=[N:4]1)(=[O:23])[CH3:22]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 79634-MethylpyridineHCID 178509486HCID 178509486, compound

Product 1

HCID 67447370(E)-1-acetyl-3-(2-(pyridin-4-yl)vinyl)-1H-indazole-6-carbonitrile

Procedure

To a mixture of 3-formyl-1H-indazole-6-carbonitrile (1.14 g, 6.67 mmol) and 4-picoline (2 mL) was added acetic anhydride (2 mL). The resulting mixture was stirred to make a homogeneous solution and then irradiated 10 min at 100° C. by microwave. After cooling to rt, the mixture was poured onto ice/H2O (50 mL) and stirred for 10 min, sonicated for 2 min, then stirred for 10 min and suction filtered to give the crude (E)-1-acetyl-3-(2-(pyridin-4-yl)vinyl)-1H-indazole-6-carbonitrile as a dark brown solid.

Workup

  1. customirradiated 10 min at 100° C. by microwave
  2. additionthe mixture was poured onto ice/H2O (50 mL)
  3. stirringstirred for 10 min
  4. customsonicated for 2 min
  5. stirringstirred for 10 min
  6. filtrationsuction filtered

Sources & evidence

ORD record
ord-0ef9ed2343ab4f6cab28f95df71d787a
Source dataset
uspto-grants-2013_07
Patent number
US08481525B2

Reaction notes

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