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

HRID 1013361
Notes
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Reaction equation

HRID 1013361 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 672062341-Benzyl-4-(4,5-dibromo-thiophen-2-yl)-pyrrolidine-3-carboxylic acid trifluoroacetate

Product 1

HCID 866043001-Benzyl-4-(4,5-dibromo-thiophen-2-yl)-pyrrolidine-3-carbonyl chloride hydrochloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344Dichloromethane
Solvent

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

  1. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-db4748893f7045d8a223bba87ade161a
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07981919B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes