Ethyl Acetate → 5-(5-Chlorobenzoxazol-6-yl)-2-pyridylamine

HRID 1036079노트

반응식

HRID 1036079 반응식
Br[C:2]1[C:10]([Cl:11])=[CH:9][C:5]2[N:6]=[CH:7][O:8][C:4]=2[CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16](B2OC(C)(C)C(C)(C)O2)=[CH:15][N:14]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC(=O)OCC>C(#N)C.O1CCOCC1.O>[Cl:11][C:10]1[C:2]([C:16]2[CH:17]=[CH:18][C:13]([NH2:12])=[N:14][CH:15]=2)=[CH:3][C:4]2[O:8][CH:7]=[N:6][C:5]=2[CH:9]=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 584872776-Bromo-5-chlorobenzoxazole

생성물 1

HCID 584869115-(5-Chlorobenzoxazol-6-yl)-2-pyridylamine수율 67.4%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 312751,4-Dioxane용매

반응 조건

온도
85 °C

실험 절차

A mixture of 6-bromo-5-chlorobenzoxazole (30) (232 mg, 1 mmol), 2-aminopyridine-5-boronic acid pinacol ester (11) (220 mg, 1 mmol), Bis(di-tret-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (A-Phos) (70 mg, 0.1 mmol) and K3PO4 (212 mg, 1 mmol) in 2 ml ACN, 2 ml dioxane, 0.5 ml H2O was bubbled with argon before heated at 85° C. for 2 h. After cooling down to r.t., the reaction mixture was taken up in ethyl acetate, washed with aq. NaHCO3 and brine, dried over Na2SO4, concentrated to dryness. The resulting red solid was dissolved in DCM and subjected to silica gel column purification using 0-100% B (A: hexane; B: EA) to furnish 165.6 mg 31 as an orange solid (yield: 67.4%)

후처리

  1. customwas bubbled with argon
  2. temperatureAfter cooling down to r.t.
  3. washwashed with aq. NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. dissolutionThe resulting red solid was dissolved in DCM
  7. customsubjected to silica gel column purification

출처 및 근거

ORD 기록
ord-68361c65d34241a982c9390e406b5357
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546403B2

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