Water → tert-butyl N-(4-bromo-2-pyridyl)-N-(cyclopropanecarbonyl)carbamate

HRID 2200111Notes

Reaction equation

HRID 2200111 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[Br:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:9]=1.CCN(CC)CC.O>C(Cl)Cl>[Br:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([N:14]([C:4]([CH:1]2[CH2:3][CH2:2]2)=[O:5])[C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 11680626tert-butyl N-(4-bromopyridin-2-yl)carbamate

Product 1

HCID 90020567tert-butyl N-(4-bromo-2-pyridyl)-N-(cyclopropanecarbonyl)carbamateYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add cyclopropanecarbonyl chloride (1.42 g, 13.68 mmol) slowly to a solution of tert-butyl N-(4-bromo-2-pyridyl)carbamate (1.24 g, 4.6 mmol), Et3N (1.38 g, 13.68 mmol) in DCM (15 mL) at 0° C. After addition, stir the reaction at room temperature for 2 hrs. Pour the reaction mixture to water (50 mL), extract with EtOAc (15 mL×3), combine the organic layers and wash with brine (100 mL). Dry over anhydrous Na2SO4; concentrate under reduced pressure to give the crude product (1.55 g) which is used without further purification. MS: (M+1): 241.0

Workup

  1. additionAfter addition
  2. customthe reaction at room temperature for 2 hrs
  3. extractionextract with EtOAc (15 mL×3)
  4. washwash with brine (100 mL)
  5. dry with materialDry over anhydrous Na2SO4
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-f7c92abafd794441b526cecb9bae2f37
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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