Trimethylsilyldiazomethane → 5-Chloro-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-pyrazine-2-carboxylic acid methyl ester

HRID 1500701ノート

反応式

HRID 1500701 の反応式
[Cl:1][C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Si:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][C:13]=2[F:22])[C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[CH3:23][Si](C=[N+]=[N-])(C)C>CO.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:23][O:9][C:8]([C:5]1[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Si:18]([CH3:19])([CH3:21])[CH3:20])=[CH:14][C:13]=2[F:22])=[N:3][C:2]([Cl:1])=[CH:7][N:6]=1)=[O:10]

参加物

6

反応物 2

HCID 167693TrimethylsilyldiazomethaneHCID 591401225-Chloro-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-pyrazine-2-carboxylic acid

生成物 1

HCID 591401805-Chloro-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-pyrazine-2-carboxylic acid methyl ester収率 71.1%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 5-chloro-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-pyrazine-2-carboxylic acid (2.95 g, 8.68 mmol) in methanol (50 mL) and toluene (100 mL) at 0° C. under N2 was added a solution of 2M trimethylsilyldiazomethane in hexanes (9.55 mL, 19.0 mmol, 2.2 eq.), and the reaction mixture was stirred at ambient temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water and brine, then dried (Na2SO4), filtered and evaporated in vacuo. The resultant residue was purified by column chromotagraphy (Si-PPC, gradient 0 to 50% ethyl acetate in hexane) to give the desired compound as a yellow solid (2.18 g, 71.1%). 1H NMR (CDCl3, 400 MHz) δ ppm 10.54 (s, 1H), 8.36 (t, J=7.86 Hz, 1H), 8.06 (s, 1H), 7.34-7.26 (m, 2H), 4.05 (s, 3H), 0.28 (s, 9H); LCMS (method D1) RT=1.38 min, [M+H]+=354.

後処理

  1. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe resultant residue was purified by column chromotagraphy (Si-PPC, gradient 0 to 50% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-fe4c3d728ea445708710d16a16f1c223
出典データセット
uspto-grants-2015_12
特許番号
US09206174B2

反応ノート

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