Cesium carbonate → N-(4-(3-Iodopyridin-2-yloxy)phenyl)benzo[D]thiazol-2-amine

HRID 1880172노트

반응식

HRID 1880172 반응식
F[C:2]1[C:7]([I:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[S:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[NH:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O>[I:8][C:7]1[C:2]([O:25][C:22]2[CH:21]=[CH:20][C:19]([NH:18][C:10]3[S:9][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=4[N:11]=3)=[CH:24][CH:23]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 70095012-Fluoro-3-iodopyridineHCID 593268134-(Benzo[d]thiazol-2-ylamino)phenol

생성물 1

HCID 59327141N-(4-(3-Iodopyridin-2-yloxy)phenyl)benzo[D]thiazol-2-amine

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

A suspension of 2-fluoro-3-iodopyridine (1.674 g, 7.51 mmol), 4-(benzo[d]thiazol-2-ylamino)phenol (2.73 g, 11.26 mmol) and cesium carbonate (4.16 g, 12.76 mmol) in N-methyl-2-pyrrolidinone (10 mL) was degassed and heated to 120° C. After 3 h 30 min, the reaction was cooled to 23° C., diluted with EtOAc (200 mL) and washed with water (100 mL) and brine (100 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluant: 0-1% methanol/dichloromethane), affording the product as an off-white solid. MS (ESI, pos. ion) m/z: 445.9 (M+1).

후처리

  1. customwas degassed
  2. temperaturethe reaction was cooled to 23° C.
  3. additiondiluted with EtOAc (200 mL)
  4. washwashed with water (100 mL) and brine (100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel chromatography (eluant: 0-1% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-c9846acf1d2a428eaf5d0596df03a630
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318718B2

반응 노트

불러오는 중…