4-Toluenesulfonyl chloride → 6-Bromo-1-tosyl-1H-pyrrolo[3,2-b]pyridine

HRID 75268Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>CN(C=O)C.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]([S:19]([C:16]3[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=3)(=[O:21])=[O:20])[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-bromo-1H-pyrrolo[3,2-b]pyridine (4.0 g, 20.3 mmol) in DMF (40 mL) at 0° C. was added sodium hydride (893 mg, 22.33 mmol). The reaction mixture was stirred at 0° C. for 30 minutes. Next, p-toluensulfonyl chloride (4.64 g, 24.26 mmol) was added, and the reaction mixture was stirred for 1 hour while warming to RT. The reaction mixture was subsequently diluted with DCM (300 mL) and washed with brine. The combined organic layers were dried over MgSO4, concentrated in vacuo, and purified by silica gel chromatography (1% to 2% MeOH/DCM) to give the title compound as a white solid (6.87 g, 96%). 1H NMR (500 MHz, CDCl3) δ ppm 8.58 (d, 1H, J=2.0 Hz), 8.43 (d, 1H, J=2.0 Hz), 7.74-7.78 (m, 3H), 7.29 (d, 2H, J=8.0 Hz), 6.83 (d, 1H, J=4.0 Hz), 2.38 (s, 3H); ESI-MS m/z [M+H]+ calc'd for C14H11BrN2O2S, 351, 353; found 351, 353.

Workup

stirringthe reaction mixture was stirred for 1 hour
temperaturewhile warming to RT
washwashed with brine
dry with materialThe combined organic layers were dried over MgSO4
concentrationconcentrated in vacuo
custompurified by silica gel chromatography (1% to 2% MeOH/DCM)

Sources & evidence

ORD record: ord-4f78bba4058e4173872ef51073006e0a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835420B2

Reaction notes

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