Dimethylformamide → 6-cyclohexyl-3-formyl-4-(methoxymethyl)-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylic acid

HRID 505789Notes

Reaction equation

HRID 505789 reaction equation
[CH:1]1([C:7]2[C:8]3[S:23][C:22]([C:24]([OH:26])=[O:25])=[CH:21][C:9]=3[N:10]([CH2:18][O:19][CH3:20])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li]C(CC)C.CN(CCN(C)C)C.CN([CH:43]=[O:44])C>C1COCC1>[CH:1]1([C:7]2[C:8]3[S:23][C:22]([C:24]([OH:26])=[O:25])=[C:21]([CH:43]=[O:44])[C:9]=3[N:10]([CH2:18][O:19][CH3:20])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 497740056-Cyclohexyl-4-(methoxymethyl)-5-phenyl-thieno[3,2-b]pyrrole-2-carboxylic acidHCID 178418400CID 53628100

Product 1

HCID 866270596-cyclohexyl-3-formyl-4-(methoxymethyl)-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylic acidYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution (0.2 M) of 6-cyclohexyl-4-(methoxymethyl)-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylic acid in THF was added dropwise to a solution (0.6 M) of sec-BuLi (3 eq.) and TMEDA (3 eq.) in THF at −78° C. After 5 min at −78° C., the resulting solution was treated with DMF (10 eq.) then was allowed to warm up at −10° C. The mixture was quenched with water and poured into aqueous HCl (0.1 N) and extracted with AcOEt. The combined organic phase was dried and concentrated to give the title compound (85%) as a solid, that was used as such.

Workup

  1. customThe mixture was quenched with water
  2. additionpoured into aqueous HCl (0.1 N)
  3. extractionextracted with AcOEt
  4. customThe combined organic phase was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e5fba91f9e37406fb1ac206db0b3c60b
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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