2-Fluoro-4-iodoaniline → 6-Chloro-3-[(2-fluoro-4-iodophenyl)amino]pyridazine-4-carboxylic acid

HRID 500514노트

반응식

HRID 500514 반응식
[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].Cl[C:11]1[N:12]=[N:13][C:14]([Cl:20])=[CH:15][C:16]=1[C:17]([OH:19])=[O:18].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1.C(OCC)(=O)C>[Cl:20][C:14]1[N:13]=[N:12][C:11]([NH:4][C:3]2[CH:5]=[CH:6][C:7]([I:9])=[CH:8][C:2]=2[F:1])=[C:16]([C:17]([OH:19])=[O:18])[CH:15]=1

참가 물질

6

반응물 3

HCID 1856942-Fluoro-4-iodoanilineHCID 4338043,6-Dichloropyridazine-4-carboxylic acidHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 248220276-Chloro-3-[(2-fluoro-4-iodophenyl)amino]pyridazine-4-carboxylic acid

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To solution of 2-fluoro-4-iodoaniline (9.21 g, 38.86 mmol) and 3,6-Dichloro-pyridazine-4-carboxylic acid (10.84 g, 64.77 mmol) in THF (80 mL) at −78° C., was added LiHMDS (5 g, 25.91 mmol). The mixture was allowed to warm to room temperature and stirred for 12 h. The mixture as diluted with ethyl acetate and washed with H2O and brine. The organic layer was dried with solid Na2SO4 and was concentrated. The resulting residue was purified by flash chromatography in silica (25% ethyl acetate-hexane) to give pure product. LC/MS [4.52 min; 394 (M+1)].

후처리

  1. washwashed with H2O and brine
  2. dry with materialThe organic layer was dried with solid Na2SO4
  3. concentrationwas concentrated
  4. customThe resulting residue was purified by flash chromatography in silica (25% ethyl acetate-hexane)
  5. customto give pure product
  6. customLC/MS [4.52 min; 394 (M+1)]

출처 및 근거

ORD 기록
ord-d3dea035d5d14531abdc06bfa73b0231
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772233B2

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