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Potassium Phosphate, Tribasic → 3-(2-Fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester

HRID 1366795
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HRID 1366795 반응식
[CH2:1]([O:3][C:4]([C:6]1[S:14][C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1OS(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)(=O)=O)=[O:5])[CH3:2].[F:32][C:33]1[CH:38]=[C:37]([S:39][CH3:40])[CH:36]=[CH:35][C:34]=1[NH2:41].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:3][C:4]([C:6]1[S:14][C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:41][C:34]1[CH:35]=[CH:36][C:37]([S:39][CH3:40])=[CH:38][C:33]=1[F:32])=[O:5])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 220256172-Fluoro-4-(methylsulfanyl)anilineHCID 597039083-(Nonafluorobutane-1-sulfonyloxy)-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester

생성물 1

HCID 597038903-(2-Fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester
수율 58.1%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

A degassed solution of 3-(nonafluorobutane-1-sulfonyloxy)-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester (0.74 g, 1.5 mmol), 2fluoro -4-methylsulfanyl-phenylamine (0.12 g, 0.76 mmol), Pd2 dba3 (0.035 g, 0.038 mmol), Xantphos (0.044 g, 0.076 mmol) and K3PO4 (0.32 g, 1.5 mmol) in toluene (10 ml) was heated at reflux for 18 hours. The reaction mixture was cooled to ambient temperature then filtered through a pad of Hyflo washing with ethyl acetate. The filtrate was concentrated in vacuo and the resultant residue subjected to flash chromatography (Si-SPE, gradient 0-10% ethyl acetate in dichloromethane) to provide the title compound as a yellow solid (0.16 g, 57%). LCMS (method B): RT=3.84 min, M+H+ 363.

후처리

  1. temperatureat reflux for 18 hours
  2. filtrationthen filtered through a pad of Hyflo
  3. washwashing with ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-d6cff3d4de6745bb9acf2fb718188cbb
출처 데이터셋
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07893085B2

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