Diisopropylethylamine → 1-{4-[(6-Bromohexyl)oxy]but-1-ynyl}-4-(cyclopentylsulfonyl)benzene

HRID 2118329Notes

Reaction equation

HRID 2118329 reaction equation
[CH:1]1([S:6]([C:9]2[CH:14]=[CH:13][C:12](Br)=[CH:11][CH:10]=2)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[Br:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][C:35]#[CH:36]>CN(C=O)C.[Cu](I)I>[Br:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][C:35]#[C:36][C:12]1[CH:13]=[CH:14][C:9]([S:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:8])=[O:7])=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 113792816-Bromohexylbut-3-ynyl etherHCID 199599631-Bromo-4-(cyclopentanesulfonyl)benzene

Product 1

HCID 691197221-{4-[(6-Bromohexyl)oxy]but-1-ynyl}-4-(cyclopentylsulfonyl)benzene

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent2×

Procedure

A stirred solution of 4-bromophenyl cyclopentyl sulfone (EP683172 A1) (0.5 g) and N,N-diisopropylethylamine (3.33 ml) in DMF (15 ml) was treated with dichlorobis(triphenylphosphine) palladium (II) (50 mg) and copper iodide (13.68 mg). The solution was heated to 70° under nitrogen and a solution of 4-[(6-bromohexyl)oxy]but-1-yne (DE 3513885 A1) and N,N-diisopropylethylamine (1.66 ml) in DMF (5 ml) was added dropwise. The mixture was stirred at 70° for 19 h. The reaction mixture was cooled to room temperature, poured onto water and extracted 3 times with EtOAc. The extracts were dried (MgSO4) and evaporated in vacuo. The residual oil was purified on a silica SPE bond elut cartridge (100 g), using a gradient of 0% to 30% diethyl ether in cyclohexane (Gradmaster™). The appropriate fractions were evaporated to give the title compound (280 mg). LCMS RT=3.93 min

Workup

  1. temperatureThe solution was heated to 70° under nitrogen
  2. additionpoured onto water
  3. extractionextracted 3 times with EtOAc
  4. dry with materialThe extracts were dried (MgSO4)
  5. customevaporated in vacuo
  6. customThe residual oil was purified on a silica SPE bond elut cartridge (100 g)
  7. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-bb3990baf77445139c829393cc7ad58a
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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