Ethyl Acetate → 5-(3,5-Dimethylbenzo[d]isoxazol-6-yl)-2-pyridylamine

HRID 1036100노트

반응식

HRID 1036100 반응식
Br[C:2]1[C:11]([CH3:12])=[CH:10][C:5]2[C:6]([CH3:9])=[N:7][O:8][C:4]=2[CH:3]=1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][N:15]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC(=O)OCC>C(#N)C.O1CCOCC1.O>[CH3:9][C:6]1[C:5]2[CH:10]=[C:11]([CH3:12])[C:2]([C:17]3[CH:18]=[CH:19][C:14]([NH2:13])=[N:15][CH:16]=3)=[CH:3][C:4]=2[O:8][N:7]=1

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 584870706-Bromo-3,5-dimethylbenzo[d]isoxazole

생성물 1

HCID 584869675-(3,5-Dimethylbenzo[d]isoxazol-6-yl)-2-pyridylamine수율 91.9%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 312751,4-Dioxane용매

반응 조건

온도
85 °C

실험 절차

A mixture of 6-bromo-3,5-dimethylbenz[d]isoxazole (104) (46 mg, 0.2 mmol), 2-aminopyridine-5-boronic acid pinacol ester (11) (66 mg, 0.3 mmol), bis(ditertbutyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (21 mg, 10% mol) and K3PO4 (64 mg, 0.3 mmol) in 0.5 ml ACN, 0.5 ml dioxane, 0.25 ml H2O was bubbled with argon before heated at 85° C. for 2.5 h. After cooling down to r.t., the reaction mixture was taken up in EA, washed with aq. NaHCO3 and brine. Org. phase was dried over Na2SO4, concentrated and then subjected to silica gel flash column chromatography (0-100% B, A: hexane; B: EA) to give 5-(3,5-dimethylbenzo[d]isoxazol-6-yl)-2-pyridylamine (105) (44 mg, yield: 91.9%, purity>90%) as yellow solid.

후처리

  1. customwas bubbled with argon
  2. temperatureAfter cooling down to r.t.
  3. washwashed with aq. NaHCO3 and brine
  4. dry with materialphase was dried over Na2SO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-09bfbf1859714d5f96b629369544a3db
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546403B2

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