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Iodo benzene diacetate → HCID 136377151、化合物

HRID 1027218
ノート
印刷プレビュー

反応式

HRID 1027218 の反応式
[F:1][C:2]([F:37])([F:36])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[N:15][C:16]([N:19]([CH3:30])[CH:20]3[CH2:25][C:24]([CH3:27])([CH3:26])[NH:23][C:22]([CH3:29])([CH3:28])[CH2:21]3)=[CH:17][CH:18]=2)=[C:9]([O:31][C:32]([F:35])([F:34])[F:33])[CH:8]=1)(=[O:5])=[O:4].C(O)(=[O:40])C.C(O)(=O)C.IC1C=CC=CC=1>CC(O)=O.CC(OC(C)=O)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:37][C:2]([F:36])([F:1])[S:3]([O:6][C:7]1[CH:8]=[C:9]([O:31][C:32]([F:33])([F:34])[F:35])[C:10]([C:13]2[N:14]=[N:15][C:16]([N:19]([CH3:30])[CH:20]3[CH2:21][C:22]([CH3:29])([CH3:28])[NH:23][C:24]([CH3:26])([CH3:27])[CH2:25]3)=[CH:17][CH:18]=2)=[C:11]([OH:40])[CH:12]=1)(=[O:4])=[O:5]
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

6

反応物 2

HCID 12217721Iodo benzene diacetateHCID 86710620HCID 86710620、化合物

生成物 1

HCID 136377151HCID 136377151、化合物

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 176Acetic Acid溶媒HCID 7918Acetic Anhydride溶媒

反応条件

温度
60 °C

実験手順

A mixture of 4-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)-3-(trifluoromethoxy)phenyl trifluoromethanesulfonate (360 mg, 0.647 mmol), iodobenzene diacetate (375 mg, 1.164 mmol) and Pd(OAc)2 (7.3 mg, 0.032 mmol) in AcOH (3.0 mL) and Ac2O (3.0 mL) was heated at 60° C. overnight. The reaction mixture was cooled to room temperature and concentrated. The residue was basified with aqueous NaHCO3 solution and extracted with DCM. The combined organic layers were dried over Na2SO4, and concentrated. The crude material was loaded onto a SCX column, washed with MeOH and diluted with 2 M NH3 in MeOH. The product-containing fractions were concentrated. Compound 3-hydroxy-4-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)-5-(trifluoromethoxy)phenyl trifluoromethanesulfonate was obtained as a yellow solid (110 mg, 28%) after flash column chromatography and HPLC purification. MS (M+1)=573.2.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. extractionextracted with DCM
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. washwashed with MeOH
  7. additiondiluted with 2 M NH3 in MeOH
  8. concentrationThe product-containing fractions were concentrated

出典と根拠

ORDレコード
ord-f6c722d8137b498782a6750d822d1bf9
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08729263B2

反応ノート

読み込み中…

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