Acetic Acid → 5-Fluoro-8-{4-[4-(5-fluoro-1-benzofuran-3-yl)-1-piperazinyl]-1-piperidinyl}quinoline

HRID 2241974노트

반응식

HRID 2241974 반응식
[F:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[F:19][C:20]1[CH:21]=[CH:22][C:23]2[O:27][CH:26]=[C:25]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[C:24]=2[CH:34]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[F:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][CH:15]([N:31]3[CH2:32][CH2:33][N:28]([C:25]4[C:24]5[CH:34]=[C:20]([F:19])[CH:21]=[CH:22][C:23]=5[O:27][CH:26]=4)[CH2:29][CH2:30]3)[CH2:14][CH2:13]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 214718555-Fluoro-3-piperazino benzofuranHCID 592048481-(5-Fluoroquinolin-8-yl)piperidin-4-one

생성물 1

HCID 120043105-Fluoro-8-{4-[4-(5-fluoro-1-benzofuran-3-yl)-1-piperazinyl]-1-piperidinyl}quinoline수율 27.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 0.200 g of 1-(5-fluoro-quinolin-8-yl)-piperidin-4-one (Example C, Step 3, 0.20 g) and 5-fluoro-3-piperazino benzofuran (Step 2, 0.20 g) in CH2Cl2 (10 mL) was added sodium triacetoxyborohydride (0.224 g) and 0.02 mL acetic acid. The reaction was stirred at room temperature overnight. It was quenched with 1N NaOH, and the product was extracted with CH2Cl2. The organic phase was washed with water and dried over magnesium sulfate. The product was filtered through 100 ML of silica gel using 50% Ethyl acetate/Hexanes then 100% Ethyl acetate to give 0.100 g of the desired product. Mp: 187-189° C.; MS (ES) m/z (relative intensity): 449 (M++−H, 100).

후처리

  1. customIt was quenched with 1N NaOH
  2. extractionthe product was extracted with CH2Cl2
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe product was filtered through 100 ML of silica gel using 50% Ethyl acetate/Hexanes

출처 및 근거

ORD 기록
ord-3efa7a0a809447ddaa80255df082a90c
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07671056B2

반응 노트

불러오는 중…