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

HRID 501042

Reaction equation

HRID 501042 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a98be02652e842e293c32253bd63e1a2
Source dataset
uspto-grants-2010_08
Patent number
US07772256B2

Linked notes

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