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 1360704ノート

反応式

HRID 1360704 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-31a43381f5494887ad630097b615bf2e
出典データセット
uspto-grants-2011_02
特許番号
US07879875B2

反応ノート

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