Potassium Carbonate → tert-Butyl {5-[(3-chloro-2,5-dioxo-4-phenyl-2,5-dihydro-1H-pyrrol-1-yl)methyl]pyridin-2-yl}carbamate

HRID 2113749Notes

Reaction equation

HRID 2113749 reaction equation
[Cl:1][C:2]1[C:3](=[O:14])[NH:4][C:5](=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[N:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:3](=[O:14])[N:4]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[N:21][CH:22]=2)[C:5](=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23030321tert-Butyl (5-(bromomethyl)pyridin-2-yl)carbamateHCID 540140893-Chloro-4-phenyl-1H-pyrrole-2,5-dione

Product 1

HCID 86607353tert-Butyl {5-[(3-chloro-2,5-dioxo-4-phenyl-2,5-dihydro-1H-pyrrol-1-yl)methyl]pyridin-2-yl}carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Chloro-4-phenyl-1H-pyrrole-2,5-dione (1.55 g, 7.47 mmol) was dissolved in DMF (25 mL) under nitrogen atmosphere and cooled in an ice-bath. tert-Butyl [5-(bromomethyl)pyridin-2-yl]carbamate (2.14 g, 7.46 mmol) was added followed by anhydrous potassium carbonate (1.03 g, 7.47 mmol)and the mixture was stirred for one and a half hours whereafter the cooling-bath was removed. The mixture was stirred for another two hours and then neutralized with 1% HCl. Water (100 mL) was added and the mixture was extracted with CH2Cl2 (50 mL×3). The extracts were combined, washed with water (100 mL×2), dried with magnesium sulphate, filtered and evaporated. The crude product (3.41 g) was used without further purification. 1H NMR (400 MHz, CDCl3): δ 8.32 (d, J=2 Hz, 1H), 7.92-7.89 (m, 3H), 7.83 (bs, 1H), 7.72 (dd, J=9, 2 Hz, 1H), 7.49-7.47 (m, 3H), 4.71 (s, 2H), 1.52 (s, 9H).

Workup

  1. temperaturecooled in an ice-bath
  2. customwas removed
  3. stirringThe mixture was stirred for another two hours
  4. additionWater (100 mL) was added
  5. extractionthe mixture was extracted with CH2Cl2 (50 mL×3)
  6. washwashed with water (100 mL×2)
  7. dry with materialdried with magnesium sulphate
  8. filtrationfiltered
  9. customevaporated
  10. customThe crude product (3.41 g) was used without further purification

Sources & evidence

ORD record
ord-156e14eb4b2f4049a20f6884734a6d94
Source dataset
uspto-grants-2008_10
Patent number
US07432288B2

Reaction notes

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