Dichloromethane → 5-(5-Hydroxy-benzofuran-2-yl)-pyridine-2-carboxylic acid amide

HRID 501042

反応式

HRID 501042 の反応式
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:17]([NH2:19])=[O:18])=[N:15][CH:16]=3)=[CH:8][C:7]=2[CH:20]=1.C(Cl)Cl.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:17]([NH2:19])=[O:18])=[N:15][CH:16]=3)=[CH:8][C:7]=2[CH:20]=1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 250148415-(5-Methoxy-benzofuran-2-yl)-pyridine-2-carboxylic acid amide

生成物 1

HCID 250149265-(5-Hydroxy-benzofuran-2-yl)-pyridine-2-carboxylic acid amide収率 37.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

5-(5-Methoxy-benzofuran-2-yl)-pyridine-2-carboxylic acid amide (0.21 mmol) was mixed with CH2Cl2 (3 mL) at 0° C. under argon atmosphere. BBr3 (1M in CH2Cl2) (1.0 mL) was added dropwise and the mixture was stirred for 2 h at rt. The mixture was hydrolysed with H2O followed by NaHCO3 (sat. aq.). The resulting mixture was filtered, and the obtained precipitate was washed with H2O and EtOAc. The solid was dried at 40° C. for 15 h under vacuum to give the title compound (20 mg). 1H NMR δ ppm 9.08 (d, 1 H) 8.33 (dd, 1 H) 8.20 (br. s., 1 H) 7.97 (d, 1 H) 7.61 (br. s., 1 H) 7.54 (s, 1 H) 7.47 (d, 1 H) 7.02 (d, 1 H) 6.85 (none, 1 H); MS m/z 255 (M+H).

後処理

  1. filtrationThe resulting mixture was filtered
  2. washthe obtained precipitate was washed with H2O and EtOAc
  3. customThe solid was dried at 40° C. for 15 h under vacuum

出典と根拠

ORDレコード
ord-a98be02652e842e293c32253bd63e1a2
出典データセット
uspto-grants-2010_08
特許番号
US07772256B2

関連ノート

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