Trityl chloride → 6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3(2H)-one

HRID 588082Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8](=[O:11])[NH:9][NH:10][C:4]=2[CH:3]=1.[C:12](Cl)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8](=[O:11])[NH:9][N:10]([C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Into a 2000-mL 4-necked round-bottom flask was placed 6-chloro-1H-pyrazolo[4,3-c]pyridin-3(2H)-one (Intermediate 1B, Step 2; 100 g, 589.73 mmol), Trt-Cl (328 g, 1.18 mol), potassium carbonate (244 g, 1.77 mol), and DMSO (1200 mL). The resulting solution was stirred for 30 h at 50° C. The reaction mixture was cooled to room temperature, then quenched by the addition of water/ice (4 L). The resulting solution was diluted with EtOAc (12 L). The solid was collected by filtration and washed with MeCN (1.5 L) to give 6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3(2H)-one, which was carried onto the next step without further purification. MS ESI calc'd. for C25H18ClN3O [M+1]+ 412. found 412.

Workup

customInto a 2000-mL 4-necked round-bottom flask was placed
temperatureThe reaction mixture was cooled to room temperature
customquenched by the addition of water/ice (4 L)
additionThe resulting solution was diluted with EtOAc (12 L)
filtrationThe solid was collected by filtration
washwashed with MeCN (1.5 L)

Sources & evidence

ORD record: ord-9e89b5c81e994839b640ed4006dda81d
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

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