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

HRID 1477271노트

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HRID 1477271 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-31e8b106c3e24af6b1f1325304239bce
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403772B2

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