1-[(2,5-Dibromothieno[2.3-b]thien-3-yl)methyl]-3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine → HCID 21978412, compound

HRID 10228Notes

Reaction equation

HRID 10228 reaction equation
Br[C:2]1[S:10][C:5]2[S:6][C:7](Br)=[CH:8][C:4]=2[C:3]=1[CH2:11][N:12]1[CH2:15][CH:14]([CH2:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:13]1.[H][H]>[Pd].CO>[F:26][C:23]1[CH:24]=[CH:25][C:20]([S:17]([CH2:16][CH:14]2[CH2:15][N:12]([CH2:11][C:3]3[C:4]4[CH:8]=[CH:7][S:6][C:5]=4[S:10][CH:2]=3)[CH2:13]2)(=[O:19])=[O:18])=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 219784041-[(2,5-Dibromothieno[2.3-b]thien-3-yl)methyl]-3-{[(4-fluorophenyl)sulfonyl]methyl}azetidineHCID 178418361HCID 178418361, compound

Product 1

HCID 21978412HCID 21978412, compoundYield 9.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-[(2,5-dibromothieno[2.3-b]thien-3-yl)methyl]-3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine (Step 4, 39 mg, 0.07 mmol) and 10% palladium on carbon (50 mg) in methanol (7 mL) was stirred under a balloon of hydrogen for 3.5 hours. The catalyst was removed by filtration through Celite®, washing with methanol after the addition of triethylamine (30 μL) to quench any HBr formed. The filtrate was concentrated in vacuo. The residue was purified by preparative TLC (50% ethyl acetate/isohexane) to give the title compound (2.5 mg). 1H NMR (500 MHz, CDCl3) δ 7.91–7.89 (2H, m), 7.34 (1H, dd, J=1.0, 5.2 Hz), 7.23 (3H, t, J=7.3 Hz), 7.10 (1H, s), 3.70 (2H, s), 3.47 (2H, t, J=7.3 Hz), 3.38 (2H, d, J=7.3 Hz), 2.96 (2H, br s), 2.88–2.82 (1H, m).

Workup

  1. customThe catalyst was removed by filtration through Celite®
  2. washwashing with methanol
  3. additionafter the addition of triethylamine (30 μL)
  4. customto quench any HBr
  5. customformed
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe residue was purified by preparative TLC (50% ethyl acetate/isohexane)

Sources & evidence

ORD record
ord-96fd61fe2c3244a199b4f9c341d9513b
Source dataset
uspto-grants-2006_08
Patent number
US07094777B2

Reaction notes

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