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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
ノート
印刷プレビュー

反応式

HRID 1366795 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d6cff3d4de6745bb9acf2fb718188cbb
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07893085B2

反応ノート

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