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

HRID 629193노트

반응식

HRID 629193 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 178454861HCID 178454861, 화합물촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-bf4c3618a45949c283206805c93a3de5
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315494B2

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