Phosphorus tribromide → 2-(Benzofuran-5-ylmethyl)pyridine

HRID 2075202

반응식

HRID 2075202 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)O)=[CH:9][C:4]=2[CH:3]=[CH:2]1.BrP(Br)Br>C(Cl)Cl.C(Cl)(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[CH:9][C:4]=2[CH:3]=[CH:2]1

참가 물질

5

반응물 2

HCID 24614Phosphorus tribromideHCID 58415302Benzofuran-5-yl(pyridin-2-yl)methanol

생성물 1

HCID 584153222-(Benzofuran-5-ylmethyl)pyridine

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

A solution of benzofuran-5-yl(pyridin-2-yl)methanol (500 mg, 2220 μmol) in DCM (10 mL) at 0° C. was treated with tribromophosphine (314 μL, 3330 μmol) and stirred for 1.5 h. The mixture was diluted with CHCl3, washed with sat. aqueous KHCO3, dried over MgSO4, and evaporated. A suspension of the crude material and 10% Pd—C (50 mg) in EtOAc (5 mL) and MeOH (3 mL) was stirred under 1 atm H2 at 24° C. for 1 h. The solids were filtered off (Celite) and washed with EtOAc. The filtrate was evaporated and purified by flash chromatography (hexanes to EtOAc to 5% MeOH in DCM) to give 2-(benzofuran-5-ylmethyl)pyridine as a yellow foam. 1H NMR (400 MHz, CD3OD) δ ppm 8.71 (br. s, 1H), 8.17 (t, J=7.6 Hz, 1H), 7.70-7.64 (m, 3H), 7.50-7.48 (m, 2H), 7.29 (d, J=8.1 Hz, 1H), 6.76 (s, 1H), 4.71 (s, 2H). MS (ESI) m/z: Calculated: 209.1; Observed: 210.0 (M++1).

후처리

  1. washwashed with sat. aqueous KHCO3
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. additionA suspension of the crude material and 10% Pd—C (50 mg) in EtOAc (5 mL) and MeOH (3 mL)
  5. stirringwas stirred under 1 atm H2 at 24° C. for 1 h
  6. filtrationThe solids were filtered off (Celite)
  7. washwashed with EtOAc
  8. customThe filtrate was evaporated
  9. custompurified by flash chromatography (hexanes to EtOAc to 5% MeOH in DCM)

출처 및 근거

ORD 기록
ord-8400e8e011cf40e69ca80bf33750e6eb
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919519B2

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