Bromine → HCID 59218663, compound

HRID 2246902Notes

Reaction equation

HRID 2246902 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([NH:19][CH3:20])[C:11]=1[C:21]#[N:22]>C(O)(=O)C>[Br:1][C:15]1[CH:14]=[C:13]([N+:16]([O-:18])=[O:17])[C:12]([NH:19][CH3:20])=[C:11]([C:21]#[N:22])[C:10]=1[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[Cl:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 59218664HCID 59218664, compound

Product 1

HCID 59218663HCID 59218663, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
86 °C

Procedure

Bromine (0.54 mL, 10.43 mmol) was added slowly to a solution of Example 8A (2.0 g, 6.96 mmol) in acetic acid (20 mL) at r.t. The reaction was heated to 86° C. and stirred for 1 h. The cooled solution was quenched with sat. bisulfite solution and extracted with EtOAc. Organics were dried (MgSO4) and concentrated in vacuo to give 2.4 g (94%) of the title compound as an orange solid. 1H NMR (400 MHz, CDCl3): δ 8.64 (s, 1H), 8.50 (br s, 1H), 7.40-7.55 (m, 3H), 7.18-7.26 (m, 1H), 3.46 (d, 3H, J=4.8 Hz). MS (ES) [m+H] calc'd for C14H9N3O2BrCl, 366, 368, 370; found 366, 368, 370.

Workup

  1. customThe cooled solution was quenched with sat. bisulfite solution
  2. extractionextracted with EtOAc
  3. dry with materialOrganics were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-480b2b2778f04d3d91cfa32871321f2e
Source dataset
uspto-grants-2010_03
Patent number
US07687638B2

Reaction notes

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