Water → Tert-butyl (6-chloro-4-iodopyridin-3-yl)(methyl)carbamate

HRID 1477271ノート

反応式

HRID 1477271 の反応式
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:9]=[N:10][C:11]([Cl:15])=[CH:12][C:13]=1[I:14])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:19]I.O>C1COCC1>[C:1]([O:5][C:6](=[O:16])[N:7]([C:8]1[CH:9]=[N:10][C:11]([Cl:15])=[CH:12][C:13]=1[I:14])[CH3:19])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53415320tert-Butyl (6-chloro-4-iodopyridin-3-yl)carbamate

生成物 1

HCID 57443399Tert-butyl (6-chloro-4-iodopyridin-3-yl)(methyl)carbamate収率 99.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To the solution of tert-butyl(6-chloro-4-iodopyridin-3-yl)carbamate (61 g, 0.172 mol) in 300 mL of anhydrous THF was added 60% NaH (7.6 g, 0.189 mol) at 0° C. under N2 atmosphere. After the addition was finished, the solution was stirred for 30 min, and then the solution of MeI (26.92 g, 0.189 mol) in 100 mL of dry THF was added. Then the solution was stirred at 0° C. for 3 hrs. TLC indicated the reaction was over. Water was added for quench, and EtOAc was added to extract twice. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated to afford 63 g of crude tert-butyl(6-chloro-4-iodopyridin-3-yl)(methyl)carbamate used into the following de-protection without the further purification.

後処理

  1. additionAfter the addition
  2. stirringThen the solution was stirred at 0° C. for 3 hrs
  3. customfor quench
  4. additionEtOAc was added
  5. extractionto extract twice
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-31e8b106c3e24af6b1f1325304239bce
出典データセット
uspto-grants-2016_08
特許番号
US09403772B2

反応ノート

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