Ethyl Acetate → HCID 66963095, compound

HRID 1363272Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:9]2[S:18][CH:19]=[CH:20][C:8]=2[CH:7]=1)=[O:5])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Br:39]N1C(=O)CCC1=O.C(OCC)(=O)C>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[N:10]([C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[C:9]2[S:18][C:19]([Br:39])=[CH:20][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 23 °C

Procedure

To 6-tert-butoxycarbonyl-6H-thieno[2,3-b]pyrrole-5-carboxylic acid ethyl ester (0.09 g, 0.31 mmol) as a solution 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, after which time the entire reaction mixture was placed directly on a silica gel column. Flash column chromatography (20% ethyl acetate in hexanes) afforded 6-tert-butoxycarbonyl-2-bromo-6H-thieno[2,3-b]pyrrole-5-carboxylic acid ethyl ester (0.04 g, 36% yield).

Workup

customafter which time the entire reaction mixture

Sources & evidence

ORD record: ord-c98d958c3926445ca943580cb5db1ca8
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884124B2

Reaction notes

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