Triethylamine → HCID 23658390, 화합물

HRID 541092노트

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HRID 541092 반응식
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

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 86645282HCID 86645282, 화합물2회HCID 178418416HCID 178418416, 화합물

생성물 1

HCID 23658390HCID 23658390, 화합물

시약·촉매·용매 2

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

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9c8cc3fab65145d4ac7a516166ca2c07
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871941B2

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