Triethylamine → 5-Cyclopropylethynyl-3-nitrothiophene-2-carboxylic acid methyl ester

HRID 532421Notes

Reaction equation

HRID 532421 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7](Br)=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])=[O:4].[C:14]([CH:16]1[CH2:18][CH2:17]1)#[CH:15].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:15]#[C:14][CH:16]2[CH2:18][CH2:17]2)=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])=[O:4]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 138823CyclopropylacetyleneHCID 57618723Methyl 5-bromo-3-nitrothiophene-2-carboxylate

Product 1

HCID 689420965-Cyclopropylethynyl-3-nitrothiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Firstly bis(triphenylphosphine)palladium(II) chloride (17.6 mg) and then copper(I) iodide (19 mg) were added to a mixture of 5-bromo-3-nitrothiophene-2-carboxylic acid methyl ester (133 mg), ethynylcyclopropane (66 mg), triethylamine (51 mg), triphenylphosphine (3.3 mg) and THF (14 mL). After one hour, the reaction mixture was partitioned between water and ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. The crude product was purified by preparative HPLC. The product with the molecular weight of 251.26 (C11H9NO4S) was obtained in this way; MS (ESI): 252 (M+H+).

Workup

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified by preparative HPLC
  5. customThe product with the molecular weight of 251.26 (C11H9NO4S) was obtained in this way

Sources & evidence

ORD record
ord-fc24ce8e6f1a43429493687898fce774
Source dataset
uspto-grants-2014_10
Patent number
US08853208B2

Reaction notes

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