Pyridine → Benzyl 3-bromo-6-{[(3-fluorophenyl)sulfonyl]amino}-2-methylbenzoate

HRID 1725901Notes

Reaction equation

HRID 1725901 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[C:6]([CH3:18])[C:5]([Br:19])=[CH:4][CH:3]=1.[F:20][C:21]1[CH:22]=[C:23]([S:27](Cl)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1.N1C=CC=CC=1>ClCCl>[Br:19][C:5]1[C:6]([CH3:18])=[C:7]([C:2]([NH:1][S:27]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([F:20])[CH:22]=2)(=[O:29])=[O:28])=[CH:3][CH:4]=1)[C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 68863679Benzyl 6-amino-3-bromo-2-methylbenzoate

Product 1

HCID 68863456Benzyl 3-bromo-6-{[(3-fluorophenyl)sulfonyl]amino}-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of Example 126B (760 mg, 2.1 mmol), 3-fluorobenzenesulfonyl chloride (600 mg, 3.1 mmol) in dichloromethane (10 mL) was treated with pyridine (0.690 mL, 8.5 mmol), stirred for 18 hours, diluted with dichloromethane (90 mL), washed with 0.5M HCl (2×100 mL) and brine, dried (Na2SO4), filtered, concentrated and purified on a Biotage silica gel cartridge (40 g) with 50-75% dichloromethane in hexanes to provide the desired product. MS (ESI(+)) m/e 478, 480 (M+H)+, 495, 497 (M+NH4)+, 500, 502 (M+Na)+; (ESI(−)) m/e 476, 478 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.23 (s, 1H), 7.64-7.35 (m, 10H), 6.83 (d, 1H), 5.25 (s, 2H), 2.19 (s, 3H).

Workup

  1. washwashed with 0.5M HCl (2×100 mL) and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on a Biotage silica gel cartridge (40 g) with 50-75% dichloromethane in hexanes

Sources & evidence

ORD record
ord-12683be24e0d4678b1adfa9ce2a4ae41
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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