Dichloromethane → HCID 86640254、化合物

HRID 422102

反応式

HRID 422102 の反応式
Br[C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:17]=[C:16](B2OC(C)(C)C(C)(C)O2)[CH:15]=[CH:14][N:13]=1.ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl.C(O)(C)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C1COCC1>[S:8]1[CH:9]=[CH:10][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([C:16]3[CH:15]=[CH:14][N:13]=[C:12]([Cl:11])[CH:17]=3)[C:7]1=2

参加物

9

反応物 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 51034082-Chloropyridine-4-boronic acid, pinacol esterHCID 120455387-Bromobenzo[b]thiophene

生成物 1

HCID 86640254HCID 86640254、化合物収率 66.3%

試薬・触媒・溶媒 4

HCID 27342152-(Di-tert-butylphosphino)biphenyl触媒HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 8028Tetrahydrofuran溶媒HCID 21906603Chloroform isopropyl alcohol溶媒

反応条件

温度
100 °C

実験手順

In a flask, combine 7-bromo-benzo[b]thiophene (1.7 g, 12 mmol), 2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (1.6 g, 7 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (285 mg, 0.3 mmol), 2-(di-tert-butylphosphino)biphenyl (63 mg, 0.2 mmol), sodium carbonate (2 M, 8 mL, 16 mmol) and THF (20 mL). Heat the mixture at 100° C. for 3 hours. Dilute the mixture with chloroform/isopropanol (3/1). Wash the solution with saturated aqueous sodium chloride. Dry over sodium sulfate. Concentrate the solution in vacuo to a dark residue. Purify by column chromatography (dichloromethane to 20% THF in dichloromethane) to afford the title compound (1.14 g, 66%) as a yellow solid. MS (ES) m/z 246 [M+1]+.

後処理

  1. customIn a flask, combine
  2. washWash the solution with saturated aqueous sodium chloride
  3. dry with materialDry over sodium sulfate
  4. concentrationConcentrate the solution in vacuo to a dark residue
  5. customPurify by column chromatography (dichloromethane to 20% THF in dichloromethane)

出典と根拠

ORDレコード
ord-50a336f664f14e72bf0fed21c70efb66
出典データセット
uspto-grants-2012_01
特許番号
US08101628B2

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