Stannane, tributyl(1-ethoxyethenyl)- → N-[6-Acetyl-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-acetamide

HRID 1497801노트

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HRID 1497801 반응식
Br[C:2]1[C:3]([CH3:25])=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[C:5]2[N:6]([N:8]=[C:9]([NH:11][C:12](=[O:14])[CH3:13])[N:10]=2)[CH:7]=1.C([Sn](CCCC)(CCCC)[C:31]([O:33]CC)=[CH2:32])CCC>CN(C=O)C.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:31]([C:2]1[C:3]([CH3:25])=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[C:5]2[N:6]([N:8]=[C:9]([NH:11][C:12](=[O:14])[CH3:13])[N:10]=2)[CH:7]=1)(=[O:33])[CH3:32]

참가 물질

5

반응물 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 86708104N-[6-Bromo-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-acetamide

생성물 1

HCID 86708111N-[6-Acetyl-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-acetamide

시약·촉매·용매 2

HCID 178419050HCID 178419050, 화합물촉매HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

N-[6-Bromo-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-acetamide (Int. 18, 1.07 g, 2.59 mmol), bis(triphenylphosphine)palladium (II) dichloride (91 mg, 0.13 mmol) and tributyl(1-ethoxyvinyl) tin were suspended in dry DMF (8 mL) and degassed with argon. The reaction mixture was heated at 120° C. for 20 min using microwave irradiation. 1 M HCl (10 mL) was added and the reaction mixture was stirred for 1 hr before being partitioned between EtOAc (100 mL) and water (100 mL). The organic layer was washed with saturated brine, then dried (Na2SO4) and concentrated in vacuo to give a yellow solid. The solid was triturated with EtOAc and the solid collected by filtration, washing with EtOAc, to give the title compound as a cream solid (680 mg).

후처리

  1. customdegassed with argon
  2. custommicrowave irradiation
  3. addition1 M HCl (10 mL) was added
  4. custombefore being partitioned between EtOAc (100 mL) and water (100 mL)
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customto give a yellow solid
  9. customThe solid was triturated with EtOAc
  10. filtrationthe solid collected by filtration
  11. washwashing with EtOAc

출처 및 근거

ORD 기록
ord-50309269f3ad48929a0f5c02abd9ee22
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199984B2

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