Water → HCID 18398677, compound

HRID 1018963Notes

Reaction equation

HRID 1018963 reaction equation
P(Br)(Br)([Br:3])=O.O[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[C:16]3[C:21](=[C:22]([P:24](=[O:31])([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27])[CH:23]=2)[N:20]=[C:19]([CH3:32])[CH:18]=[CH:17]3)=[CH:10][CH:9]=1.O>C(Cl)Cl.CN(C=O)C>[Br:3][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[C:16]3[C:21](=[C:22]([P:24](=[O:31])([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27])[CH:23]=2)[N:20]=[C:19]([CH3:32])[CH:18]=[CH:17]3)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24613Phosphorus oxybromideHCID 18398657HCID 18398657, compound

Product 1

HCID 18398677HCID 18398677, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of POBr3 (150 mg, 0.39 mmol) in CH2Cl2 (4 mL) and DMF (2 mL) was added the product of step 2 (150 mg, 0.39 mmol). The mixture was stirred at r.t. for 0.5 h. H2O was added and the mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried (anhyd. MgSO4) and concentrated in vacuo. The residue was purified by chromatography on silica gel to give 159 mg (91%) of the title compound.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (anhyd. MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f7feeb193a6e417e984744741928db75
Source dataset
uspto-grants-2002_11
Patent number
US06486141B2

Reaction notes

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