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Water → 1,1-dimethylethyl 5-(4-amino-7-iodofuro[3,2-c]pyridin-3-yl)-2,3-dihydro-1H-indole-1-carboxylate

HRID 1910076
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HRID 1910076 반응식
C1C(=O)N([I:8])C(=O)C1.[NH2:9][C:10]1[C:15]2[C:16]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23][CH2:22]4)=[CH:17][O:18][C:14]=2[CH:13]=[CH:12][N:11]=1.O>CN(C=O)C>[NH2:9][C:10]1[C:15]2[C:16]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23][CH2:22]4)=[CH:17][O:18][C:14]=2[C:13]([I:8])=[CH:12][N:11]=1
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참가 물질

5

반응물 3

HCID 962WaterHCID 120273N-Iodosuccinimide2회HCID 668240741,1-dimethylethyl 5-(4-aminofuro[3,2-c]pyridin-3-yl)-2,3-dihydro-1H-indole-1-carboxylate

생성물 1

HCID 668237261,1-dimethylethyl 5-(4-amino-7-iodofuro[3,2-c]pyridin-3-yl)-2,3-dihydro-1H-indole-1-carboxylate수율 93.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매
3회

실험 절차

A solution of NIS (0.985 g, 4.38 mmol) in DMF (20 mL) was added dropwise to a solution of 1,1-dimethylethyl 5-(4-aminofuro[3,2-c]pyridin-3-yl)-2,3-dihydro-1H-indole-1-carboxylate (1.505 g, 4.28 mmol) in DMF (20 mL) at −40° C. under Nitrogen. The mixture was stirred and allowed to slowly warm to room temperature for 17 hours. LCMS indicated about 85% conversion, so the mixture was cooled to about −30° C. and another portion of NIS (0.193 g, 0.858 mmol) in DMF (3 mL) was added dropwise. It was then allowed to slowly warm to room temperature and stirred for another 24 hours. The reaction mixture was then poured into water (ca. 200 mL) and the precipitate was collected by vacuum filtration and rinsed with Et2O (50 mL) to give 1,1-dimethylethyl 5-(4-amino-7-iodofuro[3,2-c]pyridin-3-yl)-2,3-dihydro-1H-indole-1-carboxylate (2.384 g, 4.00 mmol, 93% yield) as a tan solid. LC/MS (ES) m/z=478 [M+H]+.

후처리

  1. temperatureso the mixture was cooled to about −30° C.
  2. temperatureto slowly warm to room temperature
  3. stirringstirred for another 24 hours
  4. filtrationthe precipitate was collected by vacuum filtration
  5. washrinsed with Et2O (50 mL)

출처 및 근거

ORD 기록
ord-fe7bf380f06f4d21a6a879c3befecd15
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08598156B2

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