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

HRID 501048
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HRID 501048 반응식
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
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water
용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d98b6499593c4850ae3db2df2b789eba
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07772256B2

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