Sodium Azide → 6-Azido-4-(4-Bromo-2-fluoro-phenylamino)-pyridazine-3-carboxylic acid tert-butyl ester

HRID 558226노트

반응식

HRID 558226 반응식
[C:1]([O:5][C:6]([C:8]1[N:9]=[N:10][C:11](Cl)=[CH:12][C:13]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=1[F:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([C:8]1[N:9]=[N:10][C:11]([N:24]=[N+:25]=[N-:26])=[CH:12][C:13]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=1[F:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 2

HCID 33557Sodium AzideHCID 595194124-(4-Bromo-2-fluoro-phenylamino)-6-chloro-pyridazine-3-carboxylic acid tert-butyl ester

생성물 1

HCID 595194566-Azido-4-(4-Bromo-2-fluoro-phenylamino)-pyridazine-3-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-(4-bromo-2-fluoro-phenylamino)-6-chloro-pyridazine-3-carboxylic acid tert-butyl ester (300 mg, 034 mmol) in DMF (5 ml) under argon at room temperature is added sodium azide (96 mg, 1.48 mmol) with stirring. The reaction mixture is stirred at 50° C. for 6 hours. After cooling to room temperature, the reaction mixture is diluted with ethyl acetate and washed with water, saturated NaHCO3 (20 ml×3) and saturated NaCl (30 ml×3). The organic layer is dried over Na2SO4 and concentrated. The residue is purified by flash column chromatography to provide the desired product.

후처리

  1. stirringThe reaction mixture is stirred at 50° C. for 6 hours
  2. washwashed with water, saturated NaHCO3 (20 ml×3) and saturated NaCl (30 ml×3)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue is purified by flash column chromatography

출처 및 근거

ORD 기록
ord-03e80baf4ea2451ca1c51f9f98d83601
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063049B2

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