Iodine → 4-(2,3-Dihydro-pyrrolo[3,2-c]pyridin-1-yl)-3-fluoro-2-iodo-quinoline

HRID 457722노트

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HRID 457722 반응식
C(NC(C)C)(C)C.C([Li])CCC.[N:13]1([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[CH:24][C:23]=2[F:32])[C:21]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[CH2:15][CH2:14]1.[I:33]I>O1CCCC1.C(OCC)(=O)C.O>[N:13]1([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[C:24]([I:33])[C:23]=2[F:32])[C:21]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[CH2:15][CH2:14]1

참가 물질

8

반응물 4

HCID 807IodineHCID 7912DiisopropylamineHCID 184406484-(2,3-Dihydro-pyrrolo[3,2-c]pyridin-1-yl)-3-fluoro-quinolineHCID 178418339Butyllithium

생성물 1

HCID 184406474-(2,3-Dihydro-pyrrolo[3,2-c]pyridin-1-yl)-3-fluoro-2-iodo-quinoline수율 670.2%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매4회HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

Diisopropylamine (0.052 ml, 0.5 mmol) was added to a 50 ml round bottomed flask containing tetrahydrofuran 15. (5 ml) and magnetically stirred. The flask was cooled to 0° C. and butyllithium (0.146 ml, 2.5M solution in hexane, 0.5 mmol) was added drop wise. After 10 mins the contents were cooled to −78° C. and 4-(2,3-dihydro-pyrrolo[3,2-c]pyridin-1-yl)-3-fluoro-quinoline from Step A (0.100 g, 0.37 mmol) in 20 ml of tetrahydrofuran was added over 15 mins. The stirring was continued for an additional 2 hrs, after which iodine (0.086 g, 0.38 mmol) in 10 ml tetrahydrofuran was added. The reaction mixture was maintained at −78° C. for 2 hrs. Water and tetrahydrofuran (5 ml, 1:9) were added. The reaction mixture was diluted with ethyl acetate, washed with water and brine. Purification by column over silica gel gave pure title compound (0.97 g, 65%). MS (ES) 393.1 (M+H)+

후처리

  1. temperatureAfter 10 mins the contents were cooled to −78° C.
  2. temperatureThe reaction mixture was maintained at −78° C. for 2 hrs
  3. washwashed with water and brine
  4. customPurification by column over silica gel

출처 및 근거

ORD 기록
ord-8cba60d4953e4a7cb22fadb73003ba0d
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189733B2

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