3-Bromothiophene → HCID 18518623, compound

HRID 1369116Notes

Reaction equation

HRID 1369116 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.[Li]C(C)(C)C.[CH2:12]([N:14]([CH2:29][CH3:30])[CH2:15][CH2:16][N:17]1[C:27]2[C:22](=[C:23]([Br:28])[CH:24]=[CH:25][CH:26]=2)[C:20](=[O:21])[C:18]1=[O:19])[CH3:13].[NH4+].[Cl-]>C1COCC1>[CH2:29]([N:14]([CH2:12][CH3:13])[CH2:15][CH2:16][N:17]1[C:27]2[C:22](=[C:23]([Br:28])[CH:24]=[CH:25][CH:26]=2)[C:20]([OH:21])([C:2]2[CH:6]=[CH:5][S:4][CH:3]=2)[C:18]1=[O:19])[CH3:30]

Participants

6

Reactant 4

HCID 133833-BromothiopheneHCID 25517Ammonium ChlorideHCID 10958318HCID 10958318, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 18518623HCID 18518623, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 3-bromothiophene (105.5 mg, 2.1 eq) in anhydrous THF (2 mL) under a nitrogen atmosphere and with stirring was added t-BuLi (0.38 mL, 2.1 eq, 1.7 M in pentane) at −40° C. (bath temperature). Stirring was continued for 30 minutes after which 1-(2-diethylaminoethyl)-4-bromoisatin (100.0 mg, 3.08×10−4 mol) in anhydrous THF (2 mL) was added dropwise. The resulting red colored solution was stirred at −40° C. for 8 hours. Saturated aqueous NH4Cl (1.5 mL) was added and the reaction mixture was allowed to warm to room temperature. The mixture was extracted with EtOAc and the combined extracts were dried (anhydrous Na2SO4). After filtration the solvent was removed in vacuo. Purification was carried out by column chromatography (silica gel, eluting 1% to 2% MeOH in CHCl3) to give the title compound as a light brown foam (124.5 mg, 99%).

Workup

  1. stirringThe resulting red colored solution was stirred at −40° C. for 8 hours
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialthe combined extracts were dried (anhydrous Na2SO4)
  4. filtrationAfter filtration the solvent
  5. customwas removed in vacuo
  6. customPurification
  7. washwas carried out by column chromatography (silica gel, eluting 1% to 2% MeOH in CHCl3)

Sources & evidence

ORD record
ord-31549d43439545a9baed87308b301e8c
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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