4-Aminopyridine → HCID 11371013, 화합물

HRID 2249871노트

반응식

HRID 2249871 반응식
[F:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[N:4][C:5]2[C:10]([C:11]=1I)=[CH:9][CH:8]=[CH:7][CH:6]=2.CC(C)([O-])C.[Na+].[NH2:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1>C1(C)C=CC=CC=1.O>[F:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[N:4][C:5]2[C:10]([C:11]=1[NH:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

참가 물질

6

반응물 3

HCID 17274-AminopyridineHCID 11566815HCID 11566815, 화합물HCID 23676156Sodium t-butoxide

생성물 1

HCID 11371013HCID 11371013, 화합물수율 72%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

To a solution of 3-fluoro-2-(2-fluoro-phenyl)-4-iodo-quinoline (from Step F, 0.02 g, 0.05 mmol) in toluene (1 mL) was added S-BINAP (0.007 g, 0.01 mmol), sodium tert-butoxide (0.105 g, 1 mmol) and 4-aminopyridine (0.015 g, 0.05 mmol). The resulting mixture was degassed for 5 min., after which tris(dibenzylidineacetone) dipalladium(0) (0.0025 g, 0.0025 mmol) was added. The reaction mixture was heated to 110° C. for 48 h. and then diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in rotary evaporator. The residue was purified using HPLC over a gradient of acetonitrile and water containing 0.1% trifluoroacetic acid to yield the desired compound (0.012 g, 65%). MS (ES) 334.1 (M+H)+.

후처리

  1. customThe resulting mixture was degassed for 5 min.
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in rotary evaporator
  5. customThe residue was purified

출처 및 근거

ORD 기록
ord-455baf2234f44cd482150d2fb9399c9b
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07314939B2

반응 노트

불러오는 중…