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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
ノート
印刷プレビュー

反応式

HRID 1910076 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 120273N-Iodosuccinimide2 回HCID 668240741,1-dimethylethyl 5-(4-aminofuro[3,2-c]pyridin-3-yl)-2,3-dihydro-1H-indole-1-carboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒
3 回

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-fe7bf380f06f4d21a6a879c3befecd15
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08598156B2

反応ノート

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