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

HRID 1891599

반응식

HRID 1891599 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 592554413-(4-(4-Benzyloxy-benzyl)-pyrazol-1-yl)-pyridin-2-ylamine수율 4%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8d967b1ac2604452b74c5132b8c73629
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507530B2

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