Bromine → HCID 2336646, compound

HRID 1467821Notes

Reaction equation

HRID 1467821 reaction equation
[CH3:1][N:2]1[C:7]2[C:8](C)=[CH:9][NH:10][C:6]=2[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14].[Br:15]Br>C(O)(=O)C.O>[Br:15][C:8]1[C:7]2[N:2]([CH3:1])[C:3](=[O:14])[N:4]([CH3:13])[C:5](=[O:12])[C:6]=2[NH:10][CH:9]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 66742610HCID 66742610, compound

Product 1

HCID 2336646HCID 2336646, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Procedure

To a solution of Intermediate 1 (500 mg, 2.800 mmol) in acetic acid (5 mL) was added a solution of bromine (430 mg, 2.700 mmol) in acetic acid (5 mL) dropwise with stirring, after which water (1.2 mL) was added. The reaction mixture was stirred for another 20 min and diluted with two volumes of cold water. After 3 h, the precipitate was filtered off and washed with diethyl ether to afford 400 mg of the product as a white solid; 1H NMR (6 ppm, 300 MHz, DMSO-d6) 3.23 (s, 3H), 3.65 (s, 3H), 7.42 (s, 1H), 12.59 (br s, 1H); APCI-MS (m/z) 258.19 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred for another 20 min
  2. filtrationthe precipitate was filtered off
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-e0505ac3abdf44a290537fdf92f65a80
Source dataset
uspto-grants-2015_04
Patent number
US09000159B2

Reaction notes

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