Sodium Carbonate → (E)-8-methyl-2-(prop-1-enyl)benzo[f][1,7]naphthyridin-5-amine

HRID 340250ノート

反応式

HRID 340250 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][C:5](B2OC(C)(C)C(C)(C)O2)=[C:6]([NH:8]C(=O)OC(C)(C)C)[CH:7]=1.Cl[C:26]1[C:27]([C:35]#[N:36])=[N:28][CH:29]=[C:30](/[CH:32]=[CH:33]/[CH3:34])[CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:26]3[C:27](=[C:35]([NH2:36])[N:8]=[C:6]2[CH:7]=1)[N:28]=[CH:29][C:30](/[CH:32]=[CH:33]/[CH3:34])=[CH:31]3

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 46737997tert-Butyl (5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamateHCID 66893384(E)-3-chloro-5-(prop-1-enyl)picolinonitrile

生成物 1

HCID 66890437(E)-8-methyl-2-(prop-1-enyl)benzo[f][1,7]naphthyridin-5-amine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 21863594Toluene ethanol溶媒

実験手順

A solution of tert-butyl 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (from Example 5/Step 2) (1.0 eq.) and (E)-3-chloro-5-(prop-1-enyl)picolinonitrile (from the previous step) (1.0 eq.), tetrakis(triphenyl-phosphine)palladium (5 mol %), and 2N aqueous sodium carbonate solution (2.0 eq.) in toluene/ethanol (2:1, 0.03 M) was stirred at 100° C. overnight. After cooling to ambient temperature, the reaction content was diluted with methanol. The insoluble solids were filtered off, and the filtrate was concentrated en vacuo to obtain a crude residue. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane to give (E)-8-methyl-2-(prop-1-enyl)benzo[f][1,7]naphthyridin-5-amine as a yellow solid.

後処理

  1. customwas stirred at 100° C. overnight
  2. filtrationThe insoluble solids were filtered off
  3. concentrationthe filtrate was concentrated en vacuo
  4. customto obtain a crude residue
  5. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

出典と根拠

ORDレコード
ord-b54bef691e5148838eb6c228ce89f748
出典データセット
uspto-grants-2014_11
特許番号
US08895577B2

反応ノート

読み込み中…