4-Fluorobenzenesulfonyl chloride → HCID 68718101, compound

HRID 1159789Notes

Reaction equation

HRID 1159789 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[C:7]([CH2:14][N:15]2[CH2:20][CH2:19][N:18](C([O:23][C:24]([CH3:27])(C)C)=O)[CH2:17][CH2:16]2)[CH:6]=1.[F:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>C1COCC1>[C:24]([OH:36])(=[O:23])[CH3:27].[F:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([N:11]2[C:12]3[C:8](=[C:7]([CH2:14][N:15]4[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]4)[CH:6]=[C:5]([O:4][CH3:3])[CH:13]=3)[CH:9]=[CH:10]2)(=[O:37])=[O:36])=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 68714337HCID 68714337, compound2×

Product 1

HCID 68718101HCID 68718101, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

NaH (6 mg, 0.14 mmol, 60% in mineral oil) was added to tert-butyl 4-[(6-methoxy-1H-indol-4-yl)methyl]piperazine-1-carboxylate (10 mg, 0.029 mmol; Intermediate 40) in dry THF (1 mL). The reaction mixture was stirred for 5 min, 4-fluorobenzenesulfonyl chloride (8 mg, 0.044 mmol) in dry THF (0.5 mL) was added and the mixture was stirred over night. The reaction mixture was cooled on ice and quenched with ice and THF was evaporated. The residue was dissolved in MeOH (3 mL) and conc. HCl (0.5 mL) was added. The mixture was irradiated by microwaves at 100° C. for 300 s, the volume concentrated to ˜1.5 mL, followed of filtering and purification by preparative HPLC/UV (System A, 25-55% MeCN, 0.1% NH4OAc). The title compound (5 mg, 39%) was obtained as a white solid. MS (ESI+) for C20H22FN3O3S m/z 404 (M+H)+.

Workup

  1. stirringthe mixture was stirred over night
  2. temperatureThe reaction mixture was cooled on ice
  3. customquenched with ice and THF
  4. customwas evaporated
  5. dissolutionThe residue was dissolved in MeOH (3 mL)
  6. additionconc. HCl (0.5 mL) was added
  7. customThe mixture was irradiated by microwaves at 100° C. for 300 s
  8. concentrationthe volume concentrated to ˜1.5 mL
  9. filtrationof filtering
  10. custompurification by preparative HPLC/UV (System A, 25-55% MeCN, 0.1% NH4OAc)

Sources & evidence

ORD record
ord-44340fdeb3b844488ef2ba58c4df02a8
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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