Ethanol → HCID 86649656, compound

HRID 2367858Notes

Reaction equation

HRID 2367858 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])=[C:7]([CH3:18])[CH:6]=1)=O.[Br:19][C:20]1[CH:21]=[CH:22][C:23](N)=[N:24][CH:25]=1.[CH2:27](O)C>>[Br:19][C:20]1[CH:21]=[CH:22][C:23]2[N:24]([CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])=[C:7]([CH3:18])[CH:6]=3)[CH:27]=2)[CH:25]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 706222-Amino-5-bromopyridineHCID 17759202HCID 17759202, compound

Product 1

HCID 86649656HCID 86649656, compoundYield 28%

Procedure

N-(4-(2-bromoacetyl)-2-methylphenyl)-2,2,2-trifluoroacetamide (3.0 g; 9.26 mmol) and 5-bromopyridin-2-amine (1.5 g; 8.67 mmol) were dissolved in 20 mL ethanol. The mixture was refluxed overnight, and the solvent was removed. CH2Cl2 was added to precipitate a solid, which was filtered and washed with CH2Cl2, to afford 1.0 g (yield 28%) of product as a yellow powder. 1H NMR (300 MHz; DMSO-d6), δ 11.1 (s, 1H, NH), 9.14 (s, 1H, Ar—H), 8.60 (s, 1H, Ar—H), 7.90-7.76 (m, 4H, Ar—H), 7.46 (d, 3JHH=8.0 Hz, 1H, Ar—H), 2.19 (s, 3H, Ar—CH3).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customthe solvent was removed
  3. additionCH2Cl2 was added
  4. customto precipitate a solid, which
  5. filtrationwas filtered
  6. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-64f308b9331a4f49984f814578a62b39
Source dataset
uspto-grants-2014_04
Patent number
US08703096B2

Reaction notes

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