2-Isopropoxy-6-(trimethylstannyl)pyrazine → 3-(3-(6-isopropoxypyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,2,4-oxadiazol-5-amine

HRID 634280Notes

Reaction equation

HRID 634280 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:15]=[C:14]([NH2:16])[O:13][N:12]=3)[CH:9]=2)[N:4]([S:17]([C:20]2[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH:3]=1.[CH:27]([O:30][C:31]1[CH:36]=[N:35][CH:34]=[C:33]([Sn](C)(C)C)[N:32]=1)([CH3:29])[CH3:28]>CN(C=O)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:27]([O:30][C:31]1[N:32]=[C:33]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]4[N:15]=[C:14]([NH2:16])[O:13][N:12]=4)[CH:9]=3)[N:4]([S:17]([C:20]3[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH:3]=2)[CH:34]=[N:35][CH:36]=1)([CH3:29])[CH3:28]

Participants

6

Reactant 2

HCID 683280402-Isopropoxy-6-(trimethylstannyl)pyrazineHCID 683284823-(3-iodo-1-tosyl-1H-indol-5-yl)-1,2,4-oxadiazol-5-amine

Product 1

HCID 683285133-(3-(6-isopropoxypyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,2,4-oxadiazol-5-amineYield 59%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Argon gas was bubbled through a solution of 3-(3-iodo-1-tosyl-1H-indol-5-yl)-1,2,4-oxadiazol-5-amine (250 mg, 0.52 mmol) and 2-isopropoxy-6-(trimethylstannyl)pyrazine (188 mg, 0.62 mmol) in dry DMF (2.5 mL) for 15 min. To the mixture was added CuI (99 mg, 0.52 mmol) and Pd(PPh3)4 (60 mg, 0.052 mmol) and argon gas was further bubbled for additional 15 min. The reaction was heated at 90° C. for 1 h then cooled to RT. The reaction was quenched with ice cold water. The resulting suspension was filtered and washed with water. The solid was purified with basic alumina column chromatography (eluent: 20% EtOAc in petroleum ether) to give 3-(3-(6-isopropoxypyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,2,4-oxadiazol-5-amine (150 mg, 59%). MS (ESI, pos. ion) m/z: 491.1 (M+1).

Workup

  1. customwas further bubbled for additional 15 min
  2. temperaturethen cooled to RT
  3. customThe reaction was quenched with ice cold water
  4. filtrationThe resulting suspension was filtered
  5. washwashed with water
  6. customThe solid was purified with basic alumina column chromatography (eluent: 20% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-3dadf6a01d2842959f847e0ffd3f2fbc
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

Loading…