Methyl 5-ethyl-6-(5-(hydroxymethyl)-6-methyl-6H-thieno[2,3-b]pyrrol-2-yl)-2-methoxynicotinate → methyl 5-ethyl-6-(5-formyl-6-methyl-6H-thieno[2,3-b]pyrrol-2-yl)-2-methoxynicotinate

HRID 1481712Notes

Reaction equation

HRID 1481712 reaction equation
[CH2:1]([C:3]1[C:4]([C:15]2[S:25][C:18]3[N:19]([CH3:24])[C:20]([CH2:22][OH:23])=[CH:21][C:17]=3[CH:16]=2)=[N:5][C:6]([O:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[CH2:1]([C:3]1[C:4]([C:15]2[S:25][C:18]3[N:19]([CH3:24])[C:20]([CH:22]=[O:23])=[CH:21][C:17]=3[CH:16]=2)=[N:5][C:6]([O:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])[CH3:2]

Participants

4

Reactant 1

HCID 71281796Methyl 5-ethyl-6-(5-(hydroxymethyl)-6-methyl-6H-thieno[2,3-b]pyrrol-2-yl)-2-methoxynicotinate

Product 1

HCID 89421794methyl 5-ethyl-6-(5-formyl-6-methyl-6H-thieno[2,3-b]pyrrol-2-yl)-2-methoxynicotinateYield 82%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To solution of methyl 5-ethyl-6-(5-(hydroxymethyl)-6-methyl-6H-thieno[2,3-b]pyrrol-2-yl)-2-methoxynicotinate (0.233 g, 0.75 mmol) in DCM (8 mL) was added activated MnO2 (0.60 g+0.60 g+0.30 g, 6.20+6.20+3.10 mmol) in 3 portions with 30 min intervals. Reaction was monitored by LC/MS. Upon complete consumption of starting material MnO2 was filtered and washed with DCM. Mother liquor was concentrated affording methyl 5-ethyl-6-(5-formyl-6-methyl-6H-thieno[2,3-b]pyrrol-2-yl)-2-methoxynicotinate (0.192 g, 82%) as solid.

Workup

  1. customReaction
  2. customUpon complete consumption of starting material MnO2
  3. filtrationwas filtered
  4. washwashed with DCM
  5. concentrationMother liquor was concentrated

Sources & evidence

ORD record
ord-5d8d4a3c16724735bdacb4949a213d2e
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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