Potassium Phosphate, Tribasic → HCID 66899536、化合物

HRID 571957ノート

反応式

HRID 571957 の反応式
[NH2:1][C:2]1[C:9](Br)=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1Br.[CH:12]1(B(O)O)[CH2:14][CH2:13]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P([CH:39]2[CH2:44][CH2:43]CCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:1][C:2]1[C:9]([CH:12]2[CH2:14][CH2:13]2)=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH:43]1[CH2:44][CH2:39]1

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 27353144-Amino-3,5-dibromobenzonitrileHCID 2760897Cyclopropylboronic acid

生成物 1

HCID 66899536HCID 66899536、化合物

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

Palladium (II) acetate (814 mg, 3.62 mmol) was added to a stirred mixture of 4-amino-3,5-dibromobenzonitrile (5.00 g, 18.1 mmol), cyclopropanboronic acid (3.89 g, 45.3 mmol), potassium phosphate tribasic (23.1 g, 109 mmol) and tricyclohexylphosphine (1.02 g, 3.62 mmol) in toluene (20.0 mL) and water (1.0 mL). The resulting mixture was degassed and heated to 100° C. After 3 h, the reaction mixture was cooled to rt, diluted with water and extracted with EtOAc. The organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel (gradient elution, 0-15% EtOAc/hexanes as eluent) to afford the title compound i-7a. m/z (ES) 199 (MH)+.

後処理

  1. customThe resulting mixture was degassed
  2. temperaturethe reaction mixture was cooled to rt
  3. additiondiluted with water
  4. extractionextracted with EtOAc
  5. washThe organics were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by column chromatography on silica gel (gradient elution, 0-15% EtOAc/hexanes as eluent)

出典と根拠

ORDレコード
ord-d4654b29fac44e449bb6c6ee0d85e9cb
出典データセット
uspto-grants-2015_05
特許番号
US09029377B2

反応ノート

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