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Sodium Carbonate → 8-Methyl-2-(p-tolylethynyl)benzo[f][1,7]naphthyridin-5-amine

HRID 1259150
ノート
印刷プレビュー

反応式

HRID 1259150 の反応式
Cl[C:2]1[C:3]([C:17]#[N:18])=[N:4][CH:5]=[C:6]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[CH:7]=1.[CH3:19][C:20]1[CH:21]=[CH:22][C:23](B2OC(C)(C)C(C)(C)O2)=[C:24]([NH:26]C(=O)OC(C)(C)C)[CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.CO.C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:19][C:20]1[CH:21]=[CH:22][C:23]2=[C:2]3[C:3](=[C:17]([NH2:18])[N:26]=[C:24]2[CH:25]=1)[N:4]=[CH:5][C:6]([C:8]#[C:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)=[CH:7]3
参加物実験手順後処理出典と根拠反応ノート

参加物

8

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 668757343-Chloro-5-(p-tolylethynyl)picolinonitrile

生成物 1

HCID 668750168-Methyl-2-(p-tolylethynyl)benzo[f][1,7]naphthyridin-5-amine

試薬・触媒・溶媒 4

HCID 178418397
HCID 178418397、化合物
触媒
HCID 887Methanol溶媒
HCID 6344Dichloromethane溶媒
HCID 21863594Toluene ethanol溶媒

実験手順

A solution of 3-chloro-5-(p-tolylethynyl)picolinonitrile (from the previous step) (1.0 eq.), tert-butyl 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (from Example 5/Step 2) (1.2 eq.), tetrakis(triphenylphosphine)palladium (10 mol %), and 2N sodium carbonate aqueous solution (4.0 eq.) in toluene/ethanol (2:1, 0.2 M) was stirred at 100° C. overnight. After cooling to ambient temperature, the reaction mixture was diluted with 2% MeOH in DCM. The two phases were separated, and the aqueous layer was extracted with 2% MeOH in DCM twice. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vaccuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-40% ethyl acetate in toluene to give 8-methyl-2-(p-tolylethynyl)benzo[f][1,7]naphthyridin-5-amine.

後処理

  1. customwas stirred at 100° C. overnight
  2. customThe two phases were separated
  3. extractionthe aqueous layer was extracted with 2% MeOH in DCM twice
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated en vaccuo
  7. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

出典と根拠

ORDレコード
ord-b7fcb38fcf5340ad86486bd59941e14c
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08466167B2

反応ノート

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