Potassium Phosphate, Tribasic → 2-Methoxy-3-(2-methylthiazol-4-yl)aniline

HRID 629193ノート

反応式

HRID 629193 の反応式
Br[C:2]1[N:3]=[C:4]([CH3:7])[S:5][CH:6]=1.[CH3:8][O:9][C:10]1[C:16](B2OC(C)(C)C(C)(C)O2)=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C.[Pd](Cl)Cl.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2]>[CH3:8][O:9][C:10]1[C:16]([C:2]2[N:3]=[C:4]([CH3:7])[S:5][CH:6]=2)=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12]

参加物

7

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 27631864-Bromo-2-methyl-1,3-thiazoleHCID 754873652-Methoxy-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

生成物 1

HCID 901349262-Methoxy-3-(2-methylthiazol-4-yl)aniline収率 75.5%

試薬・触媒・溶媒 3

HCID 178454861HCID 178454861、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A stirred mixture of 4-bromo-2-methylthiazole (128 mg, 0.719 mmol), 2-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (197 mg, 0.791 mmol) and 1,1′-bis(di-tert-Butylphosphino)ferrocene palladium dichloride (14.06 mg, 0.022 mmol) in dioxane (4 mL) was degassed by bubbling nitrogen through the mixture for 5 minutes. To this was added aqueous potassium phosphate (K3PO4, 2M, 1.078 mL, 2.157 mmol) and the reaction mixture was heated to 100° C. for one hour. The reaction mixture was cooled to room temperature, then diluted with ethyl acetate (75 mL). This solution was then dried over sodium sulfate, filtered, concentrated and purified by flash chromatography, eluting with 0-100% EtOAc in hexanes. Afforded 2-methoxy-3-(2-methylthiazol-4-yl)aniline (122 mg, 0.543 mmol, 75% yield) as a yellow oil. LC retention time 0.60 [J]. m/z: 221 (MH+).

後処理

  1. customwas degassed
  2. customby bubbling nitrogen through the mixture for 5 minutes
  3. temperatureThe reaction mixture was cooled to room temperature
  4. dry with materialThis solution was then dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography
  8. washeluting with 0-100% EtOAc in hexanes

出典と根拠

ORDレコード
ord-bf4c3618a45949c283206805c93a3de5
出典データセット
uspto-grants-2016_04
特許番号
US09315494B2

反応ノート

読み込み中…