p-Bromobenzenesulfonyl chloride → Methyl 5-{[[(4-bromophenyl)sulfonyl](hexyl)amino]methyl}-2-fluorobenzoate

HRID 551991Notes

Reaction equation

HRID 551991 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([N:13]([CH2:12][C:9]2[CH:10]=[CH:11][C:2]([F:1])=[C:3]([CH:8]=2)[C:4]([O:6][CH3:7])=[O:5])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 57554492Methyl 2-fluoro-5-[(hexylamino)methyl]benzoate

Product 1

HCID 57554548Methyl 5-{[[(4-bromophenyl)sulfonyl](hexyl)amino]methyl}-2-fluorobenzoateYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-fluoro-5-[(hexylamino)methyl]benzoate in DCM (13 mL) were added 4-bromobenzenesulfonyl chloride (200 mg; 0.79 mmol) and TEA (0.13 mL; 0.94 mmol). The reaction mixture was stirred at room temperature for 2 hours under N2 atmosphere. The mixture was poured into a saturated solution of NaHCO3 and extracted with DCM (2×100 mL). The combined organic layers were then washed with a saturated solution of NH4Cl (150 mL) and with brine (150 mL), dried over magnesium sulfate, filtrated and the solvent was removed under reduced pressure. Purification by flash chromatography on silica gel (c-Hex/EtOAc, 95:5) gave 96 mg (25%) of the title compound as a colorless oil. HPLC, Rt: 5.13 min (purity=99.1%). LC/MS: M+(ESI): 486.23; 1H NMR (CDCl3) δ: 7.78 (m, 1H), 7.72 (m, 4H), 7.55 (m, 1H), 7.12 (m, 1H), 4.31 (s, 2H), 3.93 (s, 3H), 3.09 (t, J=7.5 Hz, 2H), 1.85 to 1.05 (m, 8H), 0.81 (t, J=6.9 Hz, 3H).

Workup

  1. extractionextracted with DCM (2×100 mL)
  2. washThe combined organic layers were then washed with a saturated solution of NH4Cl (150 mL) and with brine (150 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltrated
  5. customthe solvent was removed under reduced pressure
  6. customPurification by flash chromatography on silica gel (c-Hex/EtOAc, 95:5)

Sources & evidence

ORD record
ord-c4730ff378384285a1448165416c3886
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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