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Triethylamine → 6-[(3-{[Tert-butyl(dimethyl)silyl]oxy}propyl)amino]-2-chloro-5-fluoronicotinonitrile

HRID 2235937
ノート
印刷プレビュー

反応式

HRID 2235937 の反応式
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl:9][C:10]1[N:17]=[C:16]([NH:18][CH2:19][CH2:20][CH2:21][OH:22])[C:15]([F:23])=[CH:14][C:11]=1[C:12]#[N:13].ClC1N=C(Cl)C(F)=CC=1C#N.CCN(CC)CC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Si:1]([O:22][CH2:21][CH2:20][CH2:19][NH:18][C:16]1[C:15]([F:23])=[CH:14][C:11]([C:12]#[N:13])=[C:10]([Cl:9])[N:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrileHCID 866045982-Chloro-5-fluoro-6-[(3-hydroxypropyl)amino]nicotinonitrile

生成物 1

HCID 866045976-[(3-{[Tert-butyl(dimethyl)silyl]oxy}propyl)amino]-2-chloro-5-fluoronicotinonitrile収率 98%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒
HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of t-butyidimethylsilyl chloride (0.73 9, 4.79 mmol) in CH2Cl2 (21 mL) was added 2-chloro-5fluoro-6-[(3-hydroxypropyl)amino]nicotinonitrile [prepared as in Example 302] and starting from 2,6dichloro-5fluoronicotinonitrile] (1.0 g, 4.35 mmol), followed by Et3N (0.48 9, 4.79 mmol) and DMAP (0.01 g, 0.09 mmol). The resulting cloudy mixture was stirred at rt for 18 h, and then diluted with CH2Cl2. The organic layer was washed with water, dried (MgSO4), filtered, and then concentrated under reduced pressure. The product (1.47 g, 98%) was isolated after silica gel flash chromatography (2:1 hexanes/EtOAc) as a white solid. 1H NMR (400 MHz, CD3OD) δ 7.46 (d, 1H), 3.67 (t, 2H), 3.49 (t, 2H), 1.77 (qt, 2H), 0.84 (s, 9H), 0.00 (s, 6H).

後処理

  1. washThe organic layer was washed with water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-0a176ff3e7734a2a94eb8f5e34f65bf4
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07714004B2

反応ノート

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