Ammonium Chloride → HCID 67201062、化合物

HRID 509973ノート

反応式

HRID 509973 の反応式
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=[C:13]3[C:12](I)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Mg]Cl)(C)C.[C:27]([O:31][C:32](=[O:52])[N:33]([CH2:42][C:43]1[C:44]([O:50][CH3:51])=[N:45][CH:46]=[C:47]([F:49])[CH:48]=1)[C:34]1[N:39]=[CH:38][C:37]([CH:40]=[O:41])=[CH:36][N:35]=1)([CH3:30])([CH3:29])[CH3:28].[Cl-].[NH4+]>O1CCCC1>[C:27]([O:31][C:32](=[O:52])[N:33]([C:34]1[N:39]=[CH:38][C:37]([CH:40]([C:12]2[C:13]3[C:14](=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=3)[N:10]([S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[CH:11]=2)[OH:41])=[CH:36][N:35]=1)[CH2:42][C:43]1[C:44]([O:50][CH3:51])=[N:45][CH:46]=[C:47]([F:49])[CH:48]=1)([CH3:30])([CH3:28])[CH3:29]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 57963062HCID 57963062、化合物HCID 591287071H-Pyrrolo[2,3-b]pyridine, 3-iodo-5-methoxy-1-(phenylsulfonyl)-HCID 178418918HCID 178418918、化合物

生成物 1

HCID 67201062HCID 67201062、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
5 °C

実験手順

To a solution of 1-benzenesulfonyl-3-iodo-5-methoxy-1H-pyrrolo[2,3-b]pyridine (16, 1 equivalent) in 4.0 mL of tetrahydrofuran, isopropylmagnesium chloride (2.0 M in tetrahydrofuran, 1 equivalent) is added slowly at −50° C. The reaction is allowed to warm to 5° C. over 70 minutes, then cooled to −45° C. and (5-fluoro-2-methoxy-pyridin-3-ylmethyl)-(5-formyl-pyrimidin-2-yl)-carbamic acid tert-butyl ester (123, 0.78 equivalent) in 2.0 mL of tetrahydrofuran is added. The reaction is allowed to warm to room temperature over 1 hour, then poured into aqueous ammonium chloride and extracted with ethyl ether. The organic layer is dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography eluting with 20-100% ethyl acetate in hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound.

後処理

  1. temperaturecooled to −45° C.
  2. temperatureto warm to room temperature over 1 hour
  3. extractionextracted with ethyl ether
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe resulting material is purified by silica gel column chromatography
  8. washeluting with 20-100% ethyl acetate in hexane
  9. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-8652c57d4c984a7b93f59de11fd83022
出典データセット
uspto-grants-2015_08
特許番号
US09096593B2

反応ノート

読み込み中…