Bromine → HCID 68639473, compound

HRID 1809451Notes

Reaction equation

HRID 1809451 reaction equation
[Br:1]Br.[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[N:14]3[CH:23]=2)=[CH:7][CH:6]=1)#[N:4]>C(Cl)Cl.CC(O)=O>[Br:1][C:23]1[N:14]2[C:15]([C:19]([O:21][CH3:22])=[O:20])=[CH:16][CH:17]=[CH:18][C:13]2=[N:12][C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([C:3]#[N:4])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 69810781HCID 69810781, compound

Product 1

HCID 68639473HCID 68639473, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 21922555Acetic acid methylene chlorideSolvent

Procedure

Br2 (1.0 eq.) was added, dropwise, to a solution of (A2) in DCM/AcOH=1:1 (0.05 M) at RT and the reaction mixture was stirred at RT for 2 h. The reaction mixture was quenched by the addition of sat. aq. NaHCO3. The aqueous phase was separated and extracted several times with DCM. The combined organic extracts were washed with brine and dried (Na2SO4). Evaporation of the solvent gave a residue which was purified by flash column chromatography on silica using a gradient of EtOAc/Petroleum ether from 30:70 to 50:50 to yield (88%) the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6, 300K) δ 8.24 (2H, d, J=8.4 Hz), 8.00 (2H, d, J=8.6 Hz), 7.93 (1H, d, J=8.6 Hz), 7.55-7.45 (2H, m), 4.02 (3H, s). MS (ES+) C16H10BrN3O2 requires: 355/357, found: 356/358 (M+H)+.

Workup

  1. customThe reaction mixture was quenched by the addition of sat. aq. NaHCO3
  2. customThe aqueous phase was separated
  3. extractionextracted several times with DCM
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the solvent
  7. customgave a residue which
  8. customwas purified by flash column chromatography on silica using a gradient of EtOAc/Petroleum ether from 30:70 to 50:50

Sources & evidence

ORD record
ord-a0489630ccb64fffab3c2d9e9e3458dd
Source dataset
uspto-grants-2013_01
Patent number
US08362030B2

Reaction notes

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