Dichloromethane → 2-(6-Amino-pyridazin-3-yl)-benzofuran-5-ol

HRID 501048Notes

Reaction equation

HRID 501048 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]3[N:16]=[N:15][C:14]([NH2:17])=[CH:13][CH:12]=3)=[CH:8][C:7]=2[CH:18]=1.C(Cl)Cl.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>O>[NH2:17][C:14]1[N:15]=[N:16][C:11]([C:9]2[O:10][C:6]3[CH:5]=[CH:4][C:3]([OH:2])=[CH:18][C:7]=3[CH:8]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 250149286-(5-Methoxy-benzofuran-2-yl)-pyridazin-3-ylamine

Product 1

HCID 250149332-(6-Amino-pyridazin-3-yl)-benzofuran-5-olYield 25.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-(5-Methoxy-benzofuran-2-yl)-pyridazin-3-ylamine (0.14 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 extracted with EtOAc and the organic extracts were dried over Na2SO4. After filtration and evaporation of the solvent, the crude material was purified by preparative HPLC to afford the title compound as a yellow solid (8 mg). 1H NMR δ ppm 9.21 (s, 1 H) 7.74 (d, 1 H) 7.40 (d, 1 H) 7.27 (s, 1 H) 6.96 (d, 1 H) 6.86 (d, 1 H) 6.76 (dd, 1 H) 6.69 (s, 2 H); MS m/z 228 (M+H).

Workup

  1. extractionThe resulting mixture was extracted with EtOAc
  2. dry with materialthe organic extracts were dried over Na2SO4
  3. filtrationAfter filtration and evaporation of the solvent
  4. customthe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-d98b6499593c4850ae3db2df2b789eba
Source dataset
uspto-grants-2010_08
Patent number
US07772256B2

Reaction notes

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