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

HRID 1036079ノート

反応式

HRID 1036079 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
85 °C

実験手順

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%)

後処理

  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

出典と根拠

ORDレコード
ord-68361c65d34241a982c9390e406b5357
出典データセット
uspto-grants-2013_10
特許番号
US08546403B2

反応ノート

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