Pyridine → HCID 68866303, compound

HRID 1725951Notes

Reaction equation

HRID 1725951 reaction equation
[NH2:1][C:2]1[C:11]([Br:12])=[C:10]2[C:5]([CH2:6][CH2:7][C:8]([CH3:15])([CH3:14])[C:9]2=[O:13])=[CH:4][CH:3]=1.[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23](Cl)(=[O:25])=[O:24].N1C=CC=CC=1>ClCCl>[Br:12][C:11]1[C:10]2[C:9](=[O:13])[C:8]([CH3:15])([CH3:14])[CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[NH:1][S:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[F:16])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1377612-Fluorobenzenesulphonyl chlorideHCID 68863959HCID 68863959, compound

Product 1

HCID 68866303HCID 68866303, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 362B (730 mg, 2.72 mmol) and 2-fluorobenzenesulfonyl chloride (0.396 mL, 2.99 mmol) in pyridine (2.20 mL, 27.2 mmol) and dichloromethane (10 mL) was reacted as described in Example 275C to yield 0.98 g of the desired compound. MS (ESI(−)) m/e 425 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.21 (s, 1H), 7.63-7.72 (m, 2H), 7.41 (t, 1H), 7.26-7.35 (m, 3H), 2.93 (t, 2H), 1.86 (t, 2H), 1.08 (s, 6H).

Sources & evidence

ORD record
ord-72e5940dc34c49cd9383e0a8bad4d25b
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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