Boron tribromide → 2-[6-(Dimethylamino)pyridin-3-yl]-1,3-benzoxazol-5-ol

HRID 2241808노트

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HRID 2241808 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]([N:17]([CH3:19])[CH3:18])=[N:15][CH:16]=3)=[N:8][C:7]=2[CH:20]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>ClCCl>[CH3:18][N:17]([CH3:19])[C:14]1[N:15]=[CH:16][C:11]([C:9]2[O:10][C:6]3[CH:5]=[CH:4][C:3]([OH:2])=[CH:20][C:7]=3[N:8]=2)=[CH:12][CH:13]=1

참가 물질

5

반응물 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 247806565-(5-methoxy-1,3-benzoxazol-2-yl)-N,N-dimethylpyridin-2-amine

생성물 1

HCID 247806572-[6-(Dimethylamino)pyridin-3-yl]-1,3-benzoxazol-5-ol수율 23.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

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온도
0 °C

실험 절차

To a solution of 5-(5-methoxy-1,3-benzoxazol-2-yl)-N,N-dimethylpyridin-2-amine (0.368 mmol) in dichloromethane (2.0 mL) was added BBr3 in dichloromethane (1.84 mmol) at 0° C. under an atmosphere of argon and the reaction stirred for 1 h at 0° C. The reaction mixture was neutralized with NaHCO3 (sat. aq.) and dichloromethane was added. The layers were separated and the aqueous phase was extracted with dichloromethane (4×). The combined organic phases were dried (MgSO4), filtered and the solvents removed in vacuo. The crude material was purified by preparative HPLC to give 22.3 mg of the title compound as a white solid. 1H NMR δ ppm 9.44 (s, 1H), 8.83 (d, 1H), 8.13 (dd, 1H), 7.48 (d, 1H), 7.01 (d, 1H), 6.80 (d, 1H), 6.76 (dd, 1H), 3.14 (s, 6H). MS m/z (M+H) 256.

후처리

  1. additionwas added
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with dichloromethane (4×)
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvents removed in vacuo
  7. customThe crude material was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-52538839318447f79a7015f49c633089
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07670591B2

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