Triethylamine → HCID 23658390、化合物

HRID 541092ノート

反応式

HRID 541092 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH2:16][C:15]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)([C:17]([F:20])([F:19])[F:18])[O:14][N:13]=2)=[C:6]2[C:11]=1C=NC=C2.[NH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1.C([N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])C.[C]=[O:45]>C1(C)C=CC=CC=1.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]>[Cl:28][C:23]1[CH:22]=[C:21]([C:15]2([C:17]([F:20])([F:19])[F:18])[O:14][N:13]=[C:12]([C:5]3[CH:6]=[CH:11][C:2]([C:3]([NH:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=4)=[O:45])=[C:41]4[C:4]=3[CH:43]=[CH:42][N:39]=[CH:40]4)[CH2:16]2)[CH:26]=[C:25]([Cl:27])[CH:24]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 86645282HCID 86645282、化合物2 回HCID 178418416HCID 178418416、化合物

生成物 1

HCID 23658390HCID 23658390、化合物

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 1140Toluene溶媒

反応条件

温度
70 °C

実験手順

A mixture of 8-bromo-5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]isoquinoline (i.e. the product from Step C) (20 mg, 0.04 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf)) (6 mg, 0.008 mmol), 2-(aminomethyl)pyridine (17 mg, 0.16 mmol) and triethylamine (0.1 mL, 0.7 mmol) in toluene (2 mL) was purged with carbon monoxide for 15 minutes. Then the reaction vial was maintained with carbon monoxide using a balloon. The reaction mixture was stirred at 70° C. under carbon monoxide atmosphere overnight. The mixture was cooled to room temperature, filtered through a short pad of Celite® diatomaceous filter and rinsed with small amount of ethyl acetate. The filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexanes/ethyl acetate as eluent to provide the title product, a compound of the present invention, as a pale white solid (15 mg).

後処理

  1. customwas purged with carbon monoxide for 15 minutes
  2. customThen the reaction
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationfiltered through a short pad of Celite®
  5. filtrationdiatomaceous filter
  6. washrinsed with small amount of ethyl acetate
  7. concentrationThe filtrate was concentrated
  8. customthe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-9c8cc3fab65145d4ac7a516166ca2c07
出典データセット
uspto-grants-2014_10
特許番号
US08871941B2

反応ノート

読み込み中…