3-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2,6-dichloropyridine → 3-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-6-(2,6-difluorobenzyl)pyridine

HRID 1360704노트

반응식

HRID 1360704 반응식
[Si:1]([O:8][CH2:9][C:10]1[C:11]([Cl:17])=[N:12][C:13](Cl)=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br-].[F:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:21]=1[CH2:22][Zn+]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Si:1]([O:8][CH2:9][C:10]1[C:11]([Cl:17])=[N:12][C:13]([CH2:22][C:21]2[C:20]([F:19])=[CH:27][CH:26]=[CH:25][C:24]=2[F:28])=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

5

반응물 2

HCID 577003633-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2,6-dichloropyridineHCID 178505728HCID 178505728, 화합물

생성물 1

HCID 577003793-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-6-(2,6-difluorobenzyl)pyridine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,6-dichloropyridine (from Step B above, 8.5 g) in THF was added 2,6-difluorobenzylzinc bromide (90 mL, 0.5M in THF) and tetrakis(triphenylphosphine)palladium (2 g), and heated to reflux for a couple of hours until reaction completed. The mixture was cooled to room temperature and filtered through celite. The filtrate was diluted with ethyl acetate, washed with 1N NaOH, brine, dried over MgSO4 and concentrated to give title compound.

후처리

  1. temperatureheated
  2. temperatureto reflux for a couple of hours until reaction
  3. filtrationfiltered through celite
  4. additionThe filtrate was diluted with ethyl acetate
  5. washwashed with 1N NaOH, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-31a43381f5494887ad630097b615bf2e
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879875B2

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