Ethyl Acetate → HCID 59648627, compound

HRID 1363271Notes

Reaction equation

HRID 1363271 reaction equation
[S:1]1[C:5]2[NH:6][C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:8][C:4]=2[CH:3]=[CH:2]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Br:32]N1C(=O)CCC1=O.CCOC(C)=O>ClCCl>[Br:32][C:8]1[C:4]2[CH:3]=[CH:2][S:1][C:5]=2[NH:6][C:7]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 2724141Tetrabutylammonium FluorideHCID 11708220ethyl 6H-thieno[2,3-b]pyrrole-5-carboxylate

Product 1

HCID 59648627HCID 59648627, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of ethyl 6H-thieno[2,3-b]pyrrole-5-carboxylate (0.06 g, 0.31 mmol) in dichloromethane (1 mL) was added TBAF (1M THF, 0.46 mL) followed by N-bromosuccinimide (NBS) (0.07 g, 0.4 mmol). The resulting mixture was allowed to stir at 23° C. for 16 h at which time the entire reaction mixture was placed on a silica gel column. Flash column chromatography (20% EtOAc in hexanes) affords one major peak containing a mixture of 4-bromo and 2,4-dibromo products. Separation of the desired product from the byproduct by RP-HPLC (10-100% gradient 0.1% formic acid in H2O to CH3CN over 10 min) afforded ethyl 4-bromo-6H-thieno[2,3-b]pyrrole-5-carboxylate (0.03 g, 35% yield).

Workup

  1. customthe entire reaction mixture
  2. additioncontaining
  3. additiona mixture of 4-bromo and 2,4-dibromo products
  4. customSeparation of the desired product from the byproduct by RP-HPLC (10-100% gradient 0.1% formic acid in H2O to CH3CN over 10 min)

Sources & evidence

ORD record
ord-86b6420e72e848abbed301a02b163de3
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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