Triethylamine → 4-{5-(4-fluorobenzyl)-1-[1-(methylsulfonyl)azetidin-3-yl]-1H-pyrazol-3-yl}pyridine

HRID 2074100Notes

Reaction equation

HRID 2074100 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C:7]2[N:11]([CH:12]3[CH2:15][NH:14][CH2:13]3)[N:10]=[C:9]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH:8]=2)=[CH:4][CH:3]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26].C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C:7]2[N:11]([CH:12]3[CH2:13][N:14]([S:25]([CH3:24])(=[O:27])=[O:26])[CH2:15]3)[N:10]=[C:9]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67092285HCID 67092285, compound

Product 1

HCID 670924014-{5-(4-fluorobenzyl)-1-[1-(methylsulfonyl)azetidin-3-yl]-1H-pyrazol-3-yl}pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5-(4-fluorobenzyl)-1-(azetidin-3-yl)-1H-pyrazol-3-yl)pyridine (75 mg, 0.24 mmol) in CH2Cl2 (2 mL) was added methanesulfonyl chloride (19 μL, 0.24 mmol) and triethylamine (37 □L, 0.26 mmol) and the reaction mixture was stirred at room temperature for 2 hours. The solution was then loaded directly onto a pre-wetted Biotage 25M column and purified by flash chromatography (0-5% MeOH/CH2Cl2) to give the title compound as a white solid, 77 mg, 83%. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 8.58-8.67 (2 H, m), 7.59-7.69 (2 H, m), 6.97-7.13 (4 H, m), 6.49 (1 H, s), 4.84-4.98 (1 H, m), 4.45 (2 H, dd, J=8.97, 6.44 Hz), 4.05 (2 H, t, J=8.34 Hz), 4.01 (2 H, s,) 3.05 (3 H, s); m/z (APCI+) for C19H19N4O2SF 387.1 (M+H)+.

Workup

  1. custompurified by flash chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-118246c946ad41d38888413979a7c308
Source dataset
uspto-grants-2011_04
Patent number
US07919488B2

Reaction notes

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