Trityl chloride → 6-chloro-3-iodo-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridine

HRID 590773Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]2[C:9]([I:12])=[N:10][NH:11][C:4]=2[CH:3]=1.[H-].[K+].[C:15](Cl)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)(O)[O-].[Na+]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]2[C:9]([I:12])=[N:10][N:11]([C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A flask containing 6-chloro-3-iodo-4-methyl-1H-pyrazolo[4,3-c]pyridine (2.06 g, 7.02 mmol) in THF (60 mL) was cooled to 0° C. and potassium hydride (1.126 g, 14.04 mmol) was added. The reaction was stirred for 30 min followed by addition of trityl chloride (2.94 g, 10.53 mmol). The reaction mixture was warmed to room temperature and stirred for 4 h. The reaction was poured into sat. sodium bicarbonate and extracted with EtOAc. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (0-10% DCM/EtOAc) to give 6-chloro-3-iodo-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridine. MS ESI calc'd. for C26H19ClIN3 [M+1]+ 536. found 536.

Workup

temperatureThe reaction mixture was warmed to room temperature
stirringstirred for 4 h
extractionextracted with EtOAc
dry with materialThe organic phase was dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (0-10% DCM/EtOAc)

Sources & evidence

ORD record: ord-23cd76730e774fb188a26c9bb97515e1
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233979B2

Reaction notes

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