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

HRID 551985Notes

Reaction equation

HRID 551985 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:9]2[CH:10]=[CH:11][C:2]([F:1])=[C:3]([CH:8]=2)[C:4]([O:6][CH3:7])=[O:5])(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 43715358Methyl 2-fluoro-5-(hexylamino)benzoate

Product 1

HCID 57554466Methyl 5-[[(4-bromophenyl)sulfonyl](hexyl)amino]-2-fluorobenzoateYield 67.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of methyl 2-fluoro-5-(hexylamino)benzoate (800 mg; 3.16 mmol) in anhydrous DCM (50 mL) were added 4-bromobenzenesulfonylchloride. (807 mg; 3.16 mmol) and TEA (0.53 mL). The reaction mixture was stirred overnight at 25° C. under N2 atmosphere. Then the mixture was poured into a saturated solution of NaHCO3 and extracted with DCM (2×200mL). The combined organic layers were washed with a saturated solution of NH4Cl followed by brine, dried over magnesium sulfate, filtrated and the solvent was removed under reduced pressure to give a brown cream. Purification by flash chromatography using silicagel (c-Hex/EtOAc, 95:5 then 90:10):gave 1.0 g (67.4%) of the title compound as a colorless cream. HPLC, Rt: 5.23 min (purity=97.13%). LC/MS,. M+(ESI): 272.1. 1H NMR (CDCl3) δ: 7.63 (m, 2H), 7.52 (m, 1H), 7.43 (d, J=9.2 Hz, 2H), 7.25 (m, 2H), 7.13 (t, J=9.2 Hz, 1H), 3.91 (s, 3H), 3.49 (t, J=6.97 Hz, 2H), 1.25 (m, 8H), 0.85 (t, J=6.8 Hz, 3H).

Workup

  1. extractionextracted with DCM (2×200mL)
  2. washThe combined organic layers were washed with a saturated solution of NH4Cl
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltrated
  5. customthe solvent was removed under reduced pressure
  6. customto give a brown cream
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-fb37f59476e64b2f9e422914653e9e92
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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