2-Bromopyridine → 2-[(2,5-Difluorophenyl)-hydroxymethyl]pyridine

HRID 748736노트

반응식

HRID 748736 반응식
CCCCCC.C([Li])CCC.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.[F:19][C:20]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=1[CH:22]=[O:23]>O.O1CCCC1>[F:19][C:20]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=1[CH:22]([OH:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1

참가 물질

7

반응물 4

HCID 79732-BromopyridineHCID 8058HexaneHCID 1376632,5-DifluorobenzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 230286832-[(2,5-Difluorophenyl)-hydroxymethyl]pyridine

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Under an argon atmosphere, a hexane solution of n-butyl lithium (1.53M, 3.92 ml, 6 mmol) was added dropwise to a tetrahydrofuran (10 ml) solution of 2-bromopyridine (572 μl, 6 mmol) at −78° C. and the mixture was stirred for 30 minutes. To the resulting brown solution, 2,5-difluorobenzaldehyde (655 μl, 6 mmol) was added dropwise and the temperature of the mixture was gradually raised to room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate. After drying the solvent, the residue obtained by concentration under reduced pressure was purified by silica gel chromatography, whereby the title compound (120 mg, 9%) was obtained as a white solid.

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. customAfter drying the solvent
  3. customthe residue obtained by concentration under reduced pressure
  4. customwas purified by silica gel chromatography, whereby the title compound (120 mg, 9%)
  5. customwas obtained as a white solid

출처 및 근거

ORD 기록
ord-68bbf5d4e96642e1b55ea642ce0f81bb
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399775B2

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