2-Bromopropane → HCID 136338254, compound

HRID 1529433Notes

Reaction equation

HRID 1529433 reaction equation
[CH:1]([O:4][C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[C:14]3[C:20]2[O:24][C:23](=[O:25])[NH:22][N:21]=2)[CH:8]=[N:7][CH:6]=1)([CH3:3])[CH3:2].Br[CH:27]([CH3:29])[CH3:28].[H-].[Na+]>CN(C=O)C>[CH:1]([O:4][C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[C:14]3[C:20]2[O:24][C:23](=[O:25])[N:22]([CH:27]([CH3:29])[CH3:28])[N:21]=2)[CH:8]=[N:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 136338251HCID 136338251, compound

Product 1

HCID 136338254HCID 136338254, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-(5-(6-isopropoxypyrazin-2-yl)-1H-indol-3-yl)-1,3,4-oxadiazol-2(3H)-one (0.2 g, 0.5 mmol) and 2-bromo propane (0.08 g, 0.6 mmol) in DMF (1 mL) at 0° C. was added 60% sodium hydride (in mineral oil) (0.040 g, 0.1 mmol) and the reaction was stirred for 2 h at RT. The reaction was quenched with water (25 mL) and extracted with EtOAc (25 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 20% EtOAc in hexanes) to give 5-(5-(6-isopropoxypyrazin-2-yl)-1H-indol-3-yl)-3-isopropyl-1,3,4-oxadiazol-2(3H)-one (50 mg, 22%) as a white solid. MS (ESI, pos. ion) m/z: 380.0 (M+1); 1H NMR (400 MHz, CDCl3): δ ppm 8.86 (br s, 1H), 8.70 (s, 1H), 8.67 (s, 1H), 8.09 (s, 1H), 8.01 (dd, J=8.4, 1.6 Hz, 1H), 7.78 (d, J=2.8 Hz, 1H), 7.56 (d, J=8.4 Hz, 1H), 5.51-5.57 (m, 1H), 4.42-4.49 (m, 1H), 1.50 (d, J=6.8 Hz, 6H), 1.48 (d, J=6.4 Hz, 6H).

Workup

  1. customThe reaction was quenched with water (25 mL)
  2. extractionextracted with EtOAc (25 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel chromatography (eluting with 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6f6f46834a404076a4e04096143523a8
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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