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Ethanol → 4-{[(4-Benzofuran-2-yl-phenylcarbamoyl)-(4-tert-butyl-phenyl)-methyl]-amino}benzoic Acid

HRID 2371265
ノート
印刷プレビュー

反応式

HRID 2371265 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=2)[C:12](=[O:21])[NH:13][C:14]2[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)C.C([O-])([O-])=O.[Na+].[Na+].[O:41]1[C:45](B(O)O)=[CH:44][C:43]2[CH:49]=[CH:50][CH:51]=[CH:52][C:42]1=2>COCCOC.O>[O:41]1[C:42]2=[CH:52][CH:51]=[CH:50][C:49]2=[CH:43][CH:44]=[C:45]1[N:13]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:12]([CH:11]([NH:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=1)[C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=1)=[O:21]
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 702EthanolHCID 10340Sodium CarbonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 674867274-{[(4-tert-Butyl-phenyl)-(4-iodo-phenylcarbamoyl)-methyl]-amino}-benzoic Acid

生成物 1

HCID 674864684-{[(4-Benzofuran-2-yl-phenylcarbamoyl)-(4-tert-butyl-phenyl)-methyl]-amino}benzoic Acid収率 100%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 80711,2-Dimethoxyethane溶媒

実験手順

4-{[(4-tert-Butyl-phenyl)-(4-iodo-phenylcarbamoyl)-methyl]-amino}-benzoic acid acid (340 mg, 0.6 mmol) was taken up in 8 mL of DME, 4 mL of ethanol and 2 mL of water. Na2CO3 (254 mg, 2.4 mmol), PdCl2(O-tolyl)2 (61 mg, 0.0078 mmol) and benzo[B]furan-2-boronic acid (194 mg, 1.2 mmol) were then added, flushed with nitrogen and heated to reflux for 1 h. Cooled to RT, EtOAc (20 mL) was added and extracted with water (20 mL). The organic layer was washed again with water (20 mL), dried over sodium sulfate, filtered and the organic layer was removed under reduced pressure to give a white solid (120 mg, 100%). 1H NMR showed the compound to be very clean and sufficient for the following step. LCMS (M+1=599.4)

後処理

  1. customflushed with nitrogen
  2. temperatureheated
  3. temperatureto reflux for 1 h
  4. additionEtOAc (20 mL) was added
  5. extractionextracted with water (20 mL)
  6. washThe organic layer was washed again with water (20 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customthe organic layer was removed under reduced pressure

出典と根拠

ORDレコード
ord-4e08264717c24df4a777d0f553acba47
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08710236B2

反応ノート

読み込み中…

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