Triethylamine → HCID 58444571、化合物

HRID 1509767ノート

反応式

HRID 1509767 の反応式
[CH2:1]([CH:3]1[CH2:8][O:7][CH:6]([C:9]2[CH:14]=[CH:13][C:12](B3OC(C)(C)C(C)(C)O3)=[C:11]([F:24])[CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].Br[C:26]1[CH:31]=[C:30]([F:32])[C:29]([C:33]([F:48])([F:47])[O:34][C:35]2[CH:36]=[C:37]([F:46])[C:38]([C:42]([F:45])([F:44])[F:43])=[C:39]([F:41])[CH:40]=2)=[C:28]([F:49])[CH:27]=1.C(N(CC)CC)C.C(=O)([O-])O.[K+]>C1COCC1.O.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C.CC(OC)(C)C>[F:41][C:39]1[CH:40]=[C:35]([CH:36]=[C:37]([F:46])[C:38]=1[C:42]([F:43])([F:45])[F:44])[O:34][C:33]([F:47])([F:48])[C:29]1[C:28]([F:49])=[CH:27][C:26]([C:12]2[CH:13]=[CH:14][C:9]([CH:6]3[CH2:5][CH2:4][CH:3]([CH2:1][CH3:2])[CH2:8][O:7]3)=[CH:10][C:11]=2[F:24])=[CH:31][C:30]=1[F:32]

参加物

9

反応物 4

HCID 8471TriethylamineHCID 516893Potassium BicarbonateHCID 58444567HCID 58444567、化合物HCID 58444590HCID 58444590、化合物

生成物 1

HCID 58444571HCID 58444571、化合物

試薬・触媒・溶媒 4

HCID 178424406HCID 178424406、化合物触媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 15413tert-Butyl methyl ether溶媒

反応条件

温度
50 °C

実験手順

5.20 g (15.0 mmol) of 5-ethyl-2-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]tetrahydropyran are initially introduced in 35 ml of THF together with 6.93 g (15.0 mmol) of 5-((4-bromo-2,6-difluorophenyl)-difluoromethoxy)-1,3-difluoro-2-(trifluoromethyl)benzene. 590 mg (0.75 mmol) of bis(tri-o-tolylphosphine)palladium(II) chloride and 0.1 ml (0.75 mmol) of triethylamine are added. The mixture is heated to 50° C., and a solution of 2.41 g (24.0 mmol) of potassium hydrogencarbonate in 15 ml of water is added. After 3 h at this temperature, water and MTBE are added, and the organic phase is separated off. The aqueous phase is washed with MTBE, and the combined organic phases are washed with saturated sodium chloride solution and dried using sodium sulfate. The solution is concentrated to dryness, and the crude product is purified by column chromatography (SiO2, n-heptane:toluene=1:1). The further purification is carried out by recrystallisation from ethanol and n-heptane, giving 2-{4′-[(3,5-difluoro-4-trifluoromethylphenoxy)difluoromethyl]-2,3′,5′-trifluorobiphenyl-4-yl}-5-ethyltetrahydropyran as a colourless solid having an m.p. of 90° C.

後処理

  1. customthe organic phase is separated off
  2. washThe aqueous phase is washed with MTBE
  3. washthe combined organic phases are washed with saturated sodium chloride solution
  4. customdried
  5. concentrationThe solution is concentrated to dryness
  6. customthe crude product is purified by column chromatography (SiO2, n-heptane:toluene=1:1)
  7. customThe further purification
  8. customis carried out by recrystallisation from ethanol and n-heptane

出典と根拠

ORDレコード
ord-6b6fca11ffde44caa23c7ed1b1b426d8
出典データセット
uspto-grants-2012_07
特許番号
US08211513B2

反応ノート

読み込み中…