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

HRID 600653

반응식

HRID 600653 반응식
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]

참가 물질

8

반응물 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 242396-Nitroindazole2회HCID 669325916-Nitro-1h-indazole-3-carbonitrile2회HCID 178418546HCID 178418546, 화합물HCID 178526460HCID 178526460, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-91e1eae53e8348dbb7eab0384b992f95
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902217B2

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