Oxalyl chloride → 1-Benzyl-4-(4,5-dibromo-thiophen-2-yl)-pyrrolidine-3-carbonyl chloride hydrochloride

HRID 30247Notes

Reaction equation

FC(F)(F)C(O)=O.[CH2:8]([N:15]1[CH2:19][CH:18]([C:20]2[S:21][C:22]([Br:26])=[C:23]([Br:25])[CH:24]=2)[CH:17]([C:27]([OH:29])=O)[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(Cl)(=O)C([Cl:33])=O>C(Cl)Cl.CN(C=O)C>[ClH:33].[CH2:8]([N:15]1[CH2:19][CH:18]([C:20]2[S:21][C:22]([Br:26])=[C:23]([Br:25])[CH:24]=2)[CH:17]([C:27]([Cl:33])=[O:29])[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 22 °C

Procedure

The product from step c) (2.3 g, 5.18 mmol) in CH2Cl2 (26 ml) was treated with oxalyl chloride (2.3 ml, 26.3 mmol) followed by DMF (4 drops) and the mixture was stirred for 1 hour at 22° C. The solvent was evaporated in vacuo to give the crude subtitle compound as pink solid that was used without further purification.

Workup

customThe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-bd6d94572f2c49fda92c40211a4234ed
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423056B2

Reaction notes

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