Hydrochloric Acid → (Z)-tert-butyl 2-chloro-5-(2-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)-3-methoxy-2H-pyrrol-5-yl)-4H-thieno[3,2-b]pyrrole-4-carboxylate

HRID 1844587Notes

Reaction equation

HRID 1844587 reaction equation
[Cl:1][C:2]1[S:9][C:8]2[CH:7]=[C:6]([C:10]3[NH:11][C:12]([CH:17]=O)=[C:13]([O:15][CH3:16])[CH:14]=3)[N:5]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:4]=2[CH:3]=1.[CH3:26][C:27]1[NH:28][CH:29]=[C:30]([CH3:32])[CH:31]=1.Cl>CO.CCOCC>[Cl:1][C:2]1[S:9][C:8]2[CH:7]=[C:6]([C:10]3[CH:14]=[C:13]([O:15][CH3:16])/[C:12](=[CH:17]/[C:29]4[NH:28][C:27]([CH3:26])=[CH:31][C:30]=4[CH3:32])/[N:11]=3)[N:5]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 395392,4-DimethylpyrroleHCID 89500787HCID 89500787, compound

Product 1

HCID 89500931(Z)-tert-butyl 2-chloro-5-(2-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)-3-methoxy-2H-pyrrol-5-yl)-4H-thieno[3,2-b]pyrrole-4-carboxylateYield 75.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of tert-butyl 2-chloro-5-(5-formyl-4-methoxy-1H-pyrrol-2-yl)-4H-thieno[3,2-b]pyrrole-4-carboxylate (11 mg) and 2,4-dimethyl-1H-pyrrole (3.5 mg) in 1 mL of MeOH was added 2 small drops of a solution of 2 N HCl in ether. The dark-red reaction solution was stirred at r.t. for 10 min and then quenched with 3 mL of pH 7 sodium phosphate buffer solution. The product was extracted with 2×5 mL of EtOAc. The combined extracts were dried over Na2SO4, filtered, and concentrated. The residue was purified by Combiflash on a silica gel column eluted with a gradient up to 60% EtOAc/hexanes to give 10 mg of the title compound as a dark solid.

Workup

  1. customquenched with 3 mL of pH 7 sodium phosphate buffer solution
  2. extractionThe product was extracted with 2×5 mL of EtOAc
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by Combiflash on a silica gel column
  7. washeluted with a gradient up to 60% EtOAc/hexanes

Sources & evidence

ORD record
ord-e4367421ab2241da93a46884a33e3d62
Source dataset
uspto-grants-2015_02
Patent number
US08946445B2

Reaction notes

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