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

HRID 501042

반응식

HRID 501042 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a98be02652e842e293c32253bd63e1a2
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772256B2

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