HCID 59234228, compound → HCID 59234241, compound

HRID 1400206Notes

Reaction equation

HRID 1400206 reaction equation
[CH2:1]([N:5]1[CH:10]=[CH:9][C:8](O)=[C:7]([C:12]#[N:13])[C:6]1=[O:14])[CH2:2][CH2:3][CH3:4].O(Br)[Br:16].[P+3]>CN(C=O)C>[Br:16][C:8]1[CH:9]=[CH:10][N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6](=[O:14])[C:7]=1[C:12]#[N:13]

Participants

4

Reactant 2

HCID 59234228HCID 59234228, compoundHCID 178419730HCID 178419730, compound

Product 1

HCID 59234241HCID 59234241, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of intermediate 7 (39 g, 203 mmol) in DMF (600 ml) was added phosphorus(III) oxybromide (116 g, 406 mmol) and the mixture was heated at 110° C. for 1.5 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 10 (36.7 g, 72%).

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-50076fb77f4a438d996b639b3aea48bb
Source dataset
uspto-grants-2014_12
Patent number
US08906939B2

Reaction notes

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