Hydrochloric Acid → 6-Nitro-1H-indazole-3-carboxylic acid

HRID 600653

反応式

HRID 600653 の反応式
I[C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[NH:4][N:3]=1.[Cu]C#N.C(C1C2C(=CC([N+]([O-])=O)=CC=2)NN=1)#N.[N+](C1C=C2C(C=NN2)=CC=1)([O-])=[O:32].Cl.CN(C)[CH:46]=[O:47]>[OH-].[Na+]>[N+:11]([C:7]1[CH:6]=[C:5]2[C:10]([C:2]([C:46]([OH:47])=[O:32])=[N:3][NH:4]2)=[CH:9][CH:8]=1)([O-:13])=[O:12]

参加物

8

反応物 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 242396-Nitroindazole2 回HCID 669325916-Nitro-1h-indazole-3-carbonitrile2 回HCID 178418546HCID 178418546、化合物HCID 178526460HCID 178526460、化合物

生成物 1

HCID 231188596-Nitro-1H-indazole-3-carboxylic acid

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

反応条件

温度
100 °C

実験手順

A 5 mL microwave reaction vessel was charged with 3-iodo-6-nitroindazole (1 mmol), copper (I) cyanide (2 mmol) and N,N-dimethylformamide (3 mL). The vessel was sealed and subjected to microwave irradiation at 185° C. for 600 sec. The reaction mixture was partitioned between ethyl acetate (100 mL) and water (100 mL) and the mixture was filtered through Celite. The organic layer was collected, washed with brine, dried (magnesium sulfate), and concentrated to give 122 mg of a 10/1 mixture of 3-cyano-6-nitroindazole and 6-nitroindazole as a yellow solid. The 10/1 mixture of 3-cyano-6-nitroindazole and 6-nitroindazole was dissolved in 10 N sodium hydroxide and the bright orange solution was heated at 100° C. for 1 h. The mixture was allowed to cool to room temperature and carefully acidified (pH=1) with 3 N hydrochloric acid. The solid was isolated and triturated with EtOAc to provide 51 mg of 6-nitroindazole-3-carboxylic acid as a brown solid. The acid was coupled with the bicyclobase according to procedure A.

後処理

  1. customThe vessel was sealed
  2. customirradiation at 185° C. for 600 sec
  3. customThe reaction mixture was partitioned between ethyl acetate (100 mL) and water (100 mL)
  4. filtrationthe mixture was filtered through Celite
  5. customThe organic layer was collected
  6. washwashed with brine
  7. dry with materialdried (magnesium sulfate)
  8. concentrationconcentrated
  9. customto give
  10. temperatureto cool to room temperature
  11. customThe solid was isolated
  12. customtriturated with EtOAc

出典と根拠

ORDレコード
ord-91e1eae53e8348dbb7eab0384b992f95
出典データセット
uspto-grants-2011_03
特許番号
US07902217B2

関連ノート

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