Water → HCID 71736417、化合物

HRID 1471779ノート

反応式

HRID 1471779 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[C:15][C:16]2[C:21](Cl)=[CH:20][N:19]=[C:18]([C:23]3[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][C:24]=3[F:31])[CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:32].[K+].C(P(C(C)(C)C)C1(C(C)C)CC(C(C)C)=CC(C(C)C)=C1C1C=CC=CC=1)(C)(C)C.[OH2:64]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:64][C:21]3=[CH:20][N:19]=[C:18]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([NH2:30])=[O:32])=[CH:25][C:24]=4[F:31])[CH:17]=[C:16]3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 962Water2 回HCID 14797Potassium HydroxideHCID 668498352-DI-Tert-Butylphosphino-2,4,6-TriisopropylbiphenylHCID 86694573HCID 86694573、化合物

生成物 1

HCID 71736417HCID 71736417、化合物

試薬・触媒・溶媒 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

A flask is charged under Ar atmosphere with a stir bar, 4-[5-chloro-2-(4-cyano-2-fluoro-phenyl)-pyridin-4-ylethynyl]-piperidine-1-carboxylic acid tert-butyl ester (110 mg), powdered KOH (42 mg), 2-di-tert-butylphosphino-2,4,6-triisopropylbiphenyl (8 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (6 mg), water (1.5 mL), and 1,4-dioxane (3 mL). The mixture is heated to 110° C. and stirred at this temperature for 2 h. After cooling the mixture to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are washed with brine, dried (Na2SO4), and concentrated. The residue is chromatographed on silica gel [dichloromethane/(dichloromethane/methanol/7 M ammonia in methanol 50:48:2) 9:1] to give the title compound. LC (method 3): tR=1.26 min; Mass spectrum (ESI+): m/z=440 [M+H]+.

後処理

  1. additionA flask is charged under Ar atmosphere with a stir bar
  2. temperatureAfter cooling the mixture to room temperature
  3. extractionthe resulting mixture is extracted with ethyl acetate
  4. washThe combined extracts are washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel [dichloromethane/(dichloromethane/methanol/7 M ammonia in methanol 50:48:2) 9:1]

出典と根拠

ORDレコード
ord-111f8376e6174daf84391cd7100ff4c5
出典データセット
uspto-grants-2015_04
特許番号
US09012456B2

反応ノート

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