m-Chloroperbenzoic acid → HCID 66711876, compound

HRID 1262271Notes

Reaction equation

HRID 1262271 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]2=[CH:9][CH:10]=[C:11]([C:12]3[CH:13]=[C:14]([CH2:18][CH2:19][C:20]#[N:21])[CH:15]=[CH:16][CH:17]=3)[N:5]2[N:4]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)Cl>[CH3:1][S:2]([C:3]1[N:8]=[CH:7][C:6]2=[CH:9][CH:10]=[C:11]([C:12]3[CH:13]=[C:14]([CH2:18][CH2:19][C:20]#[N:21])[CH:15]=[CH:16][CH:17]=3)[N:5]2[N:4]=1)=[O:30]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 667119783-[3-(2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-propionitrile

Product 1

HCID 66711876HCID 66711876, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1148b Into a round bottom flask, 3-[3-(2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-propionitrile and Methylene chloride (50 mL) were added. m-Chloroperbenzoic acid (0.366 g, 0.00212 mol) was added portion wise over 20 minutes. The reaction was stirred at room temperature for one hour. The reaction was partitioned with DCM (200 mL) and saturated NaHCO3 (200 mL). The organic was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The solvent was removed under vacuum to give a yellow solid. The reaction mixture was purified via ISCO column chromatography with DCM and methanol as eluant (0 to 10% methanol). The collected fractions afforded 3-[3-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-propionitrile as a yellow solid (540 mg, 98%).

Workup

  1. customThe reaction was partitioned with DCM (200 mL) and saturated NaHCO3 (200 mL)
  2. customThe organic was separated
  3. washwashed with Brine
  4. dry with materialdried over Na2SO4
  5. filtrationThe solid was filtered
  6. washwashed with DCM
  7. customThe solvent was removed under vacuum
  8. customto give a yellow solid
  9. customThe reaction mixture was purified via ISCO column chromatography with DCM and methanol as eluant (0 to 10% methanol)

Sources & evidence

ORD record
ord-be8fb4f14d0b43dc94504047c0867b15
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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