HCID 10516606, compound → HCID 89700106, compound

HRID 1055691Notes

Reaction equation

HRID 1055691 reaction equation
[CH2:1]([O:3][CH:4]([O:18][CH2:19][CH3:20])[CH2:5][N:6]1[C:10]([NH2:11])=[CH:9][C:8]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[N:7]1)[CH3:2].Br[C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[C:25]([CH3:31])=[CH:24][C:23]=1[Cl:32]>>[Cl:32][C:23]1[CH:24]=[C:25]([CH3:31])[C:26]([N+:28]([O-:30])=[O:29])=[CH:27][C:22]=1[NH:11][C:10]1[N:6]([CH2:5][CH:4]([O:18][CH2:19][CH3:20])[O:3][CH2:1][CH3:2])[N:7]=[C:8]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:9]=1

Participants

3

Reactant 2

HCID 10516606HCID 10516606, compoundHCID 467382941-Bromo-2-chloro-4-methyl-5-nitrobenzene

Product 1

HCID 89700106HCID 89700106, compound

Procedure

Analogously to Example 13A/Step 1, from two reactions (273 mg and 1.58 g; 6.72 mmol in total) of the compound of Example 4A and 250 mg and 1.45 g (7.4 mmol in total) of 1-bromo-2-chloro-4-methyl-5-nitrobenzene gave, after 2 h of heating under reflux, a crude product which was purified by double chromatography on a Biotage system (in each case 50 g Snap column; mobile phase gradient hexane/ethyl acetate, from 20% ethyl acetate increasing rapidly to 100% ethyl acetate, then ethyl acetate/methanol, increasing slowly to 100% methanol). This gave 1.96 g (69% of theory) of the title compound.

Workup

  1. customgave, after 2 h
  2. temperatureof heating
  3. temperatureunder reflux
  4. customa crude product which was purified by double chromatography on a Biotage system (in each case 50 g Snap column
  5. temperaturemobile phase gradient hexane/ethyl acetate, from 20% ethyl acetate increasing rapidly to 100% ethyl acetate, then ethyl acetate/methanol, increasing slowly to 100% methanol)

Sources & evidence

ORD record
ord-8ce4c1aab4a045d6a7c65428e82fca1d
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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