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Iodine → 4-(5-fluoro-2-methoxyphenyl)-2-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

HRID 1522008
ノート
印刷プレビュー

反応式

HRID 1522008 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[N:14]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:15]=[C:16]([C:17]#[N:18])[C:9]=23)[CH:7]=1.C([N-]C(C)C)(C)C.[Li+].[I:37]I>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[N:14]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:26])[CH3:25])[C:15]([I:37])=[C:16]([C:17]#[N:18])[C:9]=23)[CH:7]=1
参加物反応条件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 807IodineHCID 2724682Lithium diisopropylamideHCID 904136554-(5-fluoro-2-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

生成物 1

HCID 904128114-(5-fluoro-2-methoxyphenyl)-2-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒
3 回

反応条件

温度
-75 °C

実験手順

A solution of Example 248B (0.7 g, 1.76 mmol) in tetrahydrofuran (50 mL) was cooled to −75° C. and treated dropwise with 2N lithium diisopropylamide in tetrahydrofuran (1.7 mL, 3.40 mmol). The mixture was stirred at −75° C. for 30 minutes and iodine (0.85 g, 3.52 mmol) in 2.5 mL tetrahydrofuran was added. The mixture was slowly brought to room temperature and quenched with aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (twice). The organic layers were concentrated and purified by column chromatography (Combi Flash Rf) (silica gel, 30% ethyl acetate in hexane) to afford the title compound. MS (ESI+) m/z 524 (M+H)+.

後処理

  1. customwas slowly brought to room temperature
  2. customquenched with aqueous ammonium chloride (100 mL)
  3. extractionextracted with ethyl acetate (twice)
  4. concentrationThe organic layers were concentrated
  5. custompurified by column chromatography (Combi Flash Rf) (silica gel, 30% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-cb38fa9446e24e90a1338f83bad414b5
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09073922B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート