2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → HCID 67364747、化合物

HRID 245757ノート

反応式

HRID 245757 の反応式
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)[CH:7]=[CH:6][C:4]=1[NH2:5].[Cl:19][C:20]1[CH:21]=[C:22]2[CH:28]=[C:27]([C:29](OC)=[O:30])[N:26]([CH3:33])[C:23]2=[N:24][CH:25]=1>O1CCCC1>[Cl:19][C:20]1[CH:21]=[C:22]2[CH:28]=[C:27]([C:29]([NH:5][C:4]3[CH:6]=[CH:7][C:8]([B:10]4[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]4)=[CH:9][C:3]=3[O:2][CH3:1])=[O:30])[N:26]([CH3:33])[C:23]2=[N:24][CH:25]=1

参加物

4

反応物 2

HCID 177502072-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 67363339HCID 67363339、化合物

生成物 1

HCID 67364747HCID 67364747、化合物収率 84%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2.073 g, 8.32 mmol) in tetrahydrofuran (dry) (20 ml) under a nitrogen atmosphere was added 2-Methylmagnesium chloride in tetrahydrofuran (4.16 ml, 8.32 mmol) and the mixture was heated at reflux for one hour. To the warm reaction mixture was added methyl 5-chloro-1-methyl-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (0.89 g, 3.96 mmol) in tetrahydrofuran (10 ml) and the resulting mixture was heated overnight. Then the reaction was cooled to room temperature and the solvent was evaporated. The residue was taken up in ethyl acetate and washed four times with 0.5 N hydrochloric acid. The organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel; gradient of heptane to heptane/ethyl acetate 1/1) to give 5-chloro-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-2-carboxamide (1.47 g).

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux for one hour
  3. customTo the warm reaction mixture
  4. temperaturethe resulting mixture was heated overnight
  5. customthe solvent was evaporated
  6. washwashed four times with 0.5 N hydrochloric acid
  7. washThe organic layer was washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by column chromatography (silica gel; gradient of heptane to heptane/ethyl acetate 1/1)

出典と根拠

ORDレコード
ord-d12add20efa84510ba6caae761c20a6b
出典データセット
uspto-grants-2014_02
特許番号
US08658794B2

反応ノート

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