Imidazole → HCID 70113495, compound

HRID 324407Notes

Reaction equation

HRID 324407 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:16]([C:17]3[C:18](=[O:24])[NH:19][C:20](=[O:23])[NH:21][CH:22]=3)[C:11]3[N:12]=[C:13]([CH3:15])[O:14][C:10]=3[CH:9]=[CH:8][C:7]=2[CH:25]=1.B(Br)(Br)Br.N1C=CN=C1.[Si:35](Cl)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]>ClCCl.CN(C)C=O>[CH3:39][C:38]([Si:35]([CH3:37])([CH3:36])[O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:16]([C:17]3[C:18](=[O:24])[NH:19][C:20](=[O:23])[NH:21][CH:22]=3)[C:11]3[N:12]=[C:13]([CH3:15])[O:14][C:10]=3[CH:9]=[CH:8][C:7]=2[CH:25]=1)([CH3:41])[CH3:40]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 25134Boron tribromide2×HCID 28928tert-Butyldimethylsilyl chlorideHCID 70113606HCID 70113606, compound

Product 1

HCID 70113495HCID 70113495, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of the product from step (vii) (1.5 g) in dichloromethane (20 ml) was added a solution of boron tribromide (1M in dichloromethane) (6 ml). The mixture was stirred at room temperature for 2 hours. A further 10 ml of boron tribromide solution was added and the mixture was stirred for 2 hours before quenching with water. The pH was adjusted to 7 with sodium bicarbonate solution and the aqueous solution extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated under reduced pressure to give a brown solid. The solid was dissolved in N,N-dimethylformamide (20 ml) and treated with imidazole (0.68 g) followed by tert-butyldimethylsilyl chloride (0.68 g). The mixture was stirred overnight then partitioned between water and ethyl acetate. The organic phase was dried (MgSO4) and evaporated under reduced pressure. Purification was by precipitation with methanol/dichloromethane/isohexane.

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. custombefore quenching with water
  3. extractionthe aqueous solution extracted with ethyl acetate
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customto give a brown solid
  7. stirringThe mixture was stirred overnight
  8. customthen partitioned between water and ethyl acetate
  9. dry with materialThe organic phase was dried (MgSO4)
  10. customevaporated under reduced pressure
  11. customPurification
  12. customwas by precipitation with methanol/dichloromethane/isohexane

Sources & evidence

ORD record
ord-fd4c256eb443470ca455fa83352a0d09
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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