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2,4-Difluoroaniline → 5-(2,6-difluorophenyl)-2-[(2,4-difluorophenyl)amino]-6H-pyrido[1,2-b]pyridazin-6-one

HRID 1454968
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HRID 1454968 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][C:10](=[O:20])[C:11]=2[C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[F:19])[N:7]=1.[O-]CCCC.[Na+].[F:27][C:28]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:29]=1[NH2:30]>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.[Fe+2]>[F:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([F:18])[C:12]=1[C:11]1[C:10](=[O:20])[CH:9]=[CH:8][N:6]2[C:5]=1[CH:4]=[CH:3][C:2]([NH:30][C:29]1[CH:31]=[CH:32][C:33]([F:35])=[CH:34][C:28]=1[F:27])=[N:7]2
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참가 물질

6

반응물 3

HCID 97092,4-DifluoroanilineHCID 23669364Sodium n-butylateHCID 575312262-chloro-5-(2,6-difluorophenyl)-6H-pyrido[1,2-b]pyridazin-6-one

생성물 1

HCID 167499415-(2,6-difluorophenyl)-2-[(2,4-difluorophenyl)amino]-6H-pyrido[1,2-b]pyridazin-6-one

시약·촉매·용매 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매
HCID 1140
Toluene
용매

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온도
80 °C

실험 절차

To a solution of 2-chloro-5-(2,6-difluorophenyl)-6H-pyrido[1,2-b]pyridazin-6-one (100 mg, 0.34 mmol) dissolved in toluene (1.5 mL) was added Pd(DBA) (3.1 mg, 0.0034 mmol), dppf (3.7 mg, 0.0068 mmol), sodium butoxide (23 mg, 0.238 mmol), and 2,4 difluoro aniline (43 mg, 0.34 mmol). The reaction was heated to 80° C. for 3 hours until complete by LCMS analysis. The reaction was passed through celite, condensed to an oil and purified via silica gel chromatography (EtOAc/CH2Cl2, MeOH) to yield the title compound.

후처리

  1. customThe reaction was passed through celite, condensed to an oil
  2. custompurified via silica gel chromatography (EtOAc/CH2Cl2, MeOH)

출처 및 근거

ORD 기록
ord-60569d70aaab452487a1c490c2ea6585
출처 데이터셋
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07482345B2

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