Dimethylformamide → HCID 57551827, compound

HRID 907333Notes

Reaction equation

HRID 907333 reaction equation
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1)[CH:11]=[CH:10]2.CN([CH:32]=[O:33])C>>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:21][CH:20]=1)[CH:11]=[C:10]2[CH:32]=[O:33]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 575517876-Bromo-2-(4-methanesulfonyl-benzyl)-2H-isoquinolin-1-one

Product 1

HCID 57551827HCID 57551827, compound

Procedure

DMF (10 mL) was cooled in an ice bath and phosphorus oxychloride (1.4 mL) added over 20 seconds. The solution was stirred for 10 minutes at room temperature then a solution of the product of step i) (2.0 g) in DMF (4 mL) was added over 5 minutes. The mixture was heated at 95° C. for 16 hours then allowed to cool and poured onto ice/water. The mixture was then extracted into ethyl acetate (100 mL) the organics combined and evaporated under reduced pressure. The residue was purified (SiO2 chromatography, eluting with 1:1 ethyl acetate:isohexane) to give the sub-titled compound (1.5 g).

Workup

  1. temperatureThe mixture was heated at 95° C. for 16 hours
  2. temperatureto cool
  3. additionpoured onto ice/water
  4. extractionThe mixture was then extracted into ethyl acetate (100 mL) the
  5. customevaporated under reduced pressure
  6. customThe residue was purified
  7. wash(SiO2 chromatography, eluting with 1:1 ethyl acetate:isohexane)

Sources & evidence

ORD record
ord-481810dd02aa4214b9f2b4c564e2f059
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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