HCID 59272911, compound → HCID 59272906, compound

HRID 2401674Notes

Reaction equation

HRID 2401674 reaction equation
[CH:1]1([CH2:4][CH2:5][N:6]2[CH:11]=[CH:10][C:9](O)=[C:8]([C:13]#[N:14])[C:7]2=[O:15])[CH2:3][CH2:2]1.O(Br)[Br:17].[P+3]>CN(C=O)C>[Br:17][C:9]1[CH:10]=[CH:11][N:6]([CH2:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)[C:7](=[O:15])[C:8]=1[C:13]#[N:14]

Participants

4

Reactant 2

HCID 59272911HCID 59272911, compoundHCID 178419730HCID 178419730, compound

Product 1

HCID 59272906HCID 59272906, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of intermediate 6 (6.0 g, 29.37 mmol) in DMF (150 ml) was added phosphorus(III) oxybromide (16.84 g, 58.75 mmol) and the mixture was heated at 110° C. for 3 hours. After cooling in an ice bath the solution was partitioned between water and EtOAc. After three extractions with EtOAc the combined organic fractions were washed with brine, dried over Na2SO4 and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; DCM as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate 9 (7.0 g, 89%).

Workup

  1. temperatureAfter cooling in an ice bath the solution
  2. customwas partitioned between water and EtOAc
  3. extractionAfter three extractions with EtOAc the combined organic fractions
  4. washwere washed with brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent evaporated in vacuo
  7. customThe crude product was purified by column chromatography (silica gel; DCM as eluent)
  8. customThe desired fractions were collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-9faa2a4c85a540229f5c2c60418dee7d
Source dataset
uspto-grants-2014_08
Patent number
US08796311B2

Reaction notes

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