Tetrahydrofuran → HCID 86681373, compound

HRID 1406672Notes

Reaction equation

HRID 1406672 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[CH2:13]Br)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:19]1([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C([O-])([O-])=O.[K+].[K+].C1COCC1>CC(C)=O>[C:1]1([S:7]([CH2:10][C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[CH2:13][N:22]2[CH2:21][CH2:20][N:19]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:24][CH2:23]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 207112Ethyl piperazine-1-acetateHCID 6038811-Bromomethyl-2-[(phenylsulfonyl)methyl]benzene

Product 1

HCID 86681373HCID 86681373, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a round-bottom flask were added 2-[(Phenylsulfonyl)methyl]benzyl bromide (4{29}, 1.0 g, 3.08 mmol, 1.0 equiv.), 10 (1.06 g, 6.16 mmol, 2.0 equiv.), K2CO3 (1.70 g, 12.32 mmol, 4.0 equiv.), and 3:2 THF:acetone (15 mL). The reaction mixture was stirred at reflux overnight. The reaction mixture was cooled to room temperature. The solid was filtered and washed with acetone. The filtrate was concentrated and purified by silica gel column chromatography (gradient, 25-50% EtOAc/hexanes) to afford 6{29} (920.1 mg, 72%) as an off-white solid. 1H-NMR (500 MHz, CDCl3): δ 7.64 (dd, 2H, J=0.5, 8.0 Hz), 7.60-7.57 (m, 1H), 7.44 (t, 2H, J=8.0 Hz), 7.21 (t, 1H, J=8.0 Hz), 7.12 (d, 2H, J=7.5 Hz), 6.98 (d, 1H, J=7.5 Hz), 4.81 (s, 2H), 4.14 (q, 2H, J=7.0), 3.31 (s, 2H), 3.15 (s, 2H), 2.50 (br s, 4H), 2.36 (br s, 4H), 1.22 (t, 3H, J=7.0 Hz). 13C-NMR (125 MHz, CDCl3): δ 170.1, 138.6, 138.1, 133.6, 132.4, 131.0, 128.8, 128.5, 128.4, 127.9, 127.3, 61.1, 60.4, 59.2, 58.9, 52.8, 52.6, 14.1.

Workup

  1. temperatureat reflux overnight
  2. filtrationThe solid was filtered
  3. washwashed with acetone
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography (gradient, 25-50% EtOAc/hexanes)
  6. customto afford 6{29} (920.1 mg, 72%) as an off-white solid

Sources & evidence

ORD record
ord-3ea0362188584fe89b8bc7c585c7b4c8
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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