Phosphorus oxychloride → HCID 90041044、化合物

HRID 1485880ノート

反応式

HRID 1485880 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[C:17](O)=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:20][C:21]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:22]=1[NH2:23].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[C:17](=[O:18])[NH:23][C:22]1[C:21]([F:20])=[CH:27][CH:26]=[CH:25][C:24]=1[F:28])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 24813Phosphorus oxychlorideHCID 796472,6-DifluoroanilineHCID 27559672-((tert-butoxy)carbonyl)-2,3-dihydro-1H-isoindole-1-carboxylic acid

生成物 1

HCID 90041044HCID 90041044、化合物収率 64.9%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a solution of 2-(tert-butoxycarbonyl)isoindoline-1-carboxylic acid (500 mg, 1.9 mmol, Eq: 1.00) and 2,6-difluoroaniline (294 mg, 2.28 mmol, Eq: 1.2) in pyridine (10 mL) at 0° C. was added POCl3 (437 mg, 266 μL, 2.85 mmol, Eq: 1.5). The reaction was warmed to RT and stirred for 2 h. The mixture was evaporated and water was added and the resulting mixture was extracted with EtOAc. The combined organics were washed with water, brine, dried with MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography to give 1-(2,6-difluoro-phenylcarbamoyl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (462 mg) as a light yellow foam.

後処理

  1. customThe mixture was evaporated
  2. additionwater was added
  3. extractionthe resulting mixture was extracted with EtOAc
  4. washThe combined organics were washed with water, brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography

出典と根拠

ORDレコード
ord-b7ffcb0902b14ffca12fd325a37c7b08
出典データセット
uspto-grants-2016_08
特許番号
US09422332B2

反応ノート

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