Chlorosuccinimide → HCID 59648574, compound

HRID 1363273Notes

Reaction equation

HRID 1363273 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.[Cl:14]N1C(=O)CCC1=O.BrC1C2C=CSC=2NC=1C(OCC)=O>>[Cl:14][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

4

Reactant 3

HCID 31398ChlorosuccinimideHCID 11708220ethyl 6H-thieno[2,3-b]pyrrole-5-carboxylateHCID 59648627HCID 59648627, compound

Product 1

HCID 59648574HCID 59648574, compoundYield 19%

Procedure

The title compound was synthesized from ethyl 6H-thieno[2,3-b]pyrrole-5-carboxylate (0.20 g, 1.02 mmol) and N-chlorosuccinimide (NCS) (0.17 g, 1.2 mmol) using the halogenation conditions to synthesize ethyl 4-bromo-6H-thieno[2,3-b]pyrrole-5-carboxylate. Separation of the desired product by RP-HPLC (10-100% gradient 0.1% formic acid in H2O to CH3CN over 10 min) afforded ethyl 4-chloro-6H-thieno[2,3-b]pyrrole-5-carboxylate (0.044 g, 19% yield). 1H NMR (400 MHz, CD3OD) δ (ppm): 9.96 (br s, 1H), 6.98 (d, J=5.4 Hz, 1H), 6.92 (d, J=5.4 Hz, 1H), 4.43 (q, J=7.1 Hz, 2H), 1.43 (t, J=7.1 Hz, 3H). 13C NMR (101 MHz, CD3OD) δ (ppm): 161.1, 136.8, 131.3, 124.4, 123.5, 121.5, 116.5, 61.3, 14.6. LCMS m/e 230 (M+H).

Workup

  1. customSeparation of the desired product by RP-HPLC (10-100% gradient 0.1% formic acid in H2O to CH3CN over 10 min)

Sources & evidence

ORD record
ord-11d3b881780a4c838c0282e977bebf45
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

Loading…