Sodium Iodide → 1-(Diphenylmethyl)-3-{[(2-fluorophenyl)sulfonyl]methyl}azetidine

HRID 10212Notes

Reaction equation

HRID 10212 reaction equation
CS(O[CH2:6][CH:7]1[CH2:10][N:9]([CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8]1)(=O)=O.[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31]([O-:33])=[O:32].[Na+].[I-].[Na+]>CN(C)C=O>[C:18]1([CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:9]2[CH2:8][CH:7]([CH2:6][S:31]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[F:24])(=[O:33])=[O:32])[CH2:10]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 21978370(1-Benzhydrylazetidin-3-yl)methyl methanesulfonateHCID 23682181Sodium 2-fluorobenzene-1-sulfinate

Product 1

HCID 219783651-(Diphenylmethyl)-3-{[(2-fluorophenyl)sulfonyl]methyl}azetidineYield 36.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[1-(Diphenylmethyl)azetidin-3-yl]methyl methanesulfonate [Example 1, step 1] (3.15 g, 9.50 mmol), sodium 2-fluorobenzenesulfinate (2.65 g, 14.3 mmol) and sodium iodide (2.18 g, 14.5 mmol) were reacted in dimethylformamide (50 mL) by the procedure of Example I Step 3a to afford the title compound (1.37 g, 36%); 1H NMR (500 MHz, CDCl3) δ 2.80–2.88 (3H, m), 3.33 (2H, t, J=7.0 Hz), 3.57 (2H, d, J=6.9 Hz), 4.28 (1H, s), 7.16 (2H, t, J=7.3 Hz), 7.20–7.26 (5H, m), 7.29–7.35 (5H, m), 7.61–7.65 (1H, m), 7.86–7.90 (1H, m); 19F NMR (471 MHz, CDCl3) δ −108.9; m/z (ES+) 396 ([M+H]+, 100%).

Sources & evidence

ORD record
ord-ef56ae228a4c40cd8eb87cf6971b20ef
Source dataset
uspto-grants-2006_08
Patent number
US07094777B2

Reaction notes

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