N,N'-Dimethylethylenediamine → 1-Isopropyl-3-methyl-6-(methylsulfonyl)-1H-indole-4-carboxylic acid

HRID 516773ノート

反応式

HRID 516773 の反応式
Br[C:2]1[CH:3]=[C:4]([C:15]([O:17]C)=[O:16])[C:5]2[C:6]([CH3:14])=[CH:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[CH3:19][S:20]([OH:22])=[O:21].CNCCNC>CS(C)=O>[CH:11]([N:8]1[C:9]2[CH:10]=[C:2]([S:20]([CH3:19])(=[O:22])=[O:21])[CH:3]=[C:4]([C:15]([OH:17])=[O:16])[C:5]=2[C:6]([CH3:14])=[CH:7]1)([CH3:13])[CH3:12]

参加物

5

反応物 3

HCID 8070N,N'-DimethylethylenediamineHCID 87251Methanesulfinic acidHCID 67464634methyl 6-bromo-1-isopropyl-3-methyl-1H-indole-4-carboxylate

生成物 1

HCID 674652371-Isopropyl-3-methyl-6-(methylsulfonyl)-1H-indole-4-carboxylic acid収率 25.3%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
165 °C

実験手順

To a 30-mL microwave tube were added methyl 6-bromo-3-methyl-1-(1-methylethyl)-1H-indole-4-carboxylate (490 mg, 1.580 mmol), methanesulfinic acid (212 mg, 2.054 mmol), DMSO (7 mL), N,N′-dimethyl-1,2-ethanediamine (18.10 mg, 0.205 mmol), and the mixture was degassed for 5 min by bubbling N2. Copper(I) trifluoromethanesulfonate benzene complex (63.6 mg, 0.126 mmol) was added and the tube was sealed. The mixture was heated at 165° C. overnight with stirring. The mixture was allowed to cool, filtered and purified using reverse-phase HPLC (Gemini 5u C18(2) 100A, AXIA; 30×100 mm 5 micron; 30 mL/min, 30% ACN/H2O, 0.1% formic acid to 60% ACN/H2O, 0.1% formic acid) to give the title compound (118 mg, 25%) as a white solid. 1H NMR (400 MHz, DMSO-d6) ppm 1.47 (d, J=8.00 Hz, 6H), 2.30-2.41 (m, 3H), 4.94 (quin, J=6.63 Hz, 1H), 7.80 (s, 1H), 7.88 (d, J=1.77 Hz, 1H), 8.24 (d, J=1.52 Hz, 1H), 13.17 (br. s., 1H). MS: (M+H)+=296.3.

後処理

  1. customthe mixture was degassed for 5 min
  2. customby bubbling N2
  3. additionCopper(I) trifluoromethanesulfonate benzene complex (63.6 mg, 0.126 mmol) was added
  4. customthe tube was sealed
  5. temperatureto cool
  6. filtrationfiltered
  7. custompurified

出典と根拠

ORDレコード
ord-26960f4824e245f99b2688231eb2fe79
出典データセット
uspto-grants-2015_08
特許番号
US09114141B2

反応ノート

読み込み中…