Acetic Acid → HCID 57377429, compound

HRID 1478123Notes

Reaction equation

HRID 1478123 reaction equation
Br[CH:2]([C:27]1[O:31][C:30]([C:32]2[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][CH:33]=2)=[N:29][N:28]=1)[CH:3](Br)[C:4]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[C:7]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][N:17]=2)=[N:6][N:5]=1.C(O[K])(C)(C)C.C(O)(=O)C.C(OCC)(=O)C>C1C=CC=CC=1>[Cl:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[N:8]1[C:7]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][N:17]=2)=[N:6][N:5]=[C:4]1[C:3]#[C:2][C:27]1[O:31][C:30]([C:32]2[CH:33]=[CH:34][C:35]([C:36]#[N:37])=[CH:38][CH:39]=2)=[N:29][N:28]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 67960442HCID 67960442, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 57377429HCID 57377429, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(5-{1,2-Dibromo-2-[4-(2-chloro-phenyl)-5-(5-methanesulfonyl-pyridin-2-yl)-4H-[1,2,4]triazol-3-yl]-ethyl}-[1,3,4]oxadiazol-2-yl)-benzonitrile 2 (0.1 g, 0.19 mmol) in benzene (10 mL) was added tBuOK (0.05 g, 0.28 mmol) portionwise at 0° C. The mixture was stirred at 0° C. for 1 h, treated with diluted acetic acid and ethyl acetate, washed with H2O, dried over Na2SO4 and concentrated. The residue was subjected to FCC (50-100% ethyl acetate/hexanes) to afford 4-{5-[4-(2-Chloro-phenyl)-5-(5-methanesulfonyl-pyridin-2-yl)-4H-[1,2,4]triazol-3-ylethynyl]-[1,3,4]oxadiazol-2-yl}-benzonitrile. Yield: 0.03 g, 39%.

Workup

  1. washwashed with H2O
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f63a5c84d3c949938dcfdf68c6d8a155
Source dataset
uspto-grants-2016_08
Patent number
US09403812B2

Reaction notes

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