Tri-o-tolylphosphine → 3-(4-(4-Benzyloxy-benzyl)-pyrazol-1-yl)-pyridin-2-ylamine

HRID 1693835

反応式

HRID 1693835 の反応式
Br[C:2]1[CH:3]=[N:4][N:5]([C:7]2[C:8]([NH2:13])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=1.[CH2:14]([O:21][C:22]1[CH:41]=[CH:40][C:25]([CH2:26][Sn](CCCC)(CCCC)CCCC)=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN1CCCC1=O>[CH2:14]([O:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:26][C:2]2[CH:3]=[N:4][N:5]([C:7]3[C:8]([NH2:13])=[N:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=2)=[CH:40][CH:41]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

6

反応物 3

HCID 80271Tri-o-tolylphosphineHCID 592550903-(4-Bromo-pyrazol-1-yl)-pyridin-2-ylamineHCID 59255482(4-Benzyloxy-benzyl)-tributyl-stannane

生成物 1

HCID 592554413-(4-(4-Benzyloxy-benzyl)-pyrazol-1-yl)-pyridin-2-ylamine収率 5.2%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

To a mixture of 3-(4-bromo-pyrazol-1-yl)-pyridin-2-ylamine (34 mg, 0.14 mmol) described in Manufacturing Example 39-1-4, (4-benzyloxy-benzyl)-tributyl-stannane (84 mg, 0.17 mmol) described in Manufacturing Example 39-2-1 and N-methylpyrrolidinone (1.5 mL) were added tri-o-tolylphosphine (17 mg, 0.057 mmol) and palladium (II) acetate (3.2 mg, 0.014 mmol) at room temperature, which was stirred for 5 hours at 120° C. The reaction mixture was cooled to room temperature, and filtered after addition of an aqueous potassium fluoride solution and ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by reverse-phase high performance liquid chromatography (using an acetonitrile-water mobile phase containing 0.1% trifluoroacetic acid) to obtain the title compound (2.6 mg, 4%) as a trifluoroacetic acid salt.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. additionafter addition of an aqueous potassium fluoride solution and ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous sodium chloride
  6. customthe solvent was evaporated under a reduced pressure
  7. customThe residue was purified by reverse-phase high performance liquid chromatography (
  8. additioncontaining 0.1% trifluoroacetic acid)

出典と根拠

ORDレコード
ord-c4ee0af6d90e43149f09d907e6e73136
出典データセット
uspto-grants-2012_04
特許番号
US08158657B2

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