Methanol → methyl 6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridine-3-carboxylate

HRID 571372Notes

Reaction equation

[CH3:1][C:2]([O-:4])=[O:3].[Na+].[Cl:6][C:7]1[N:12]=[CH:11][C:10]2C(I)=[N:14][N:15]([C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:9]=2[CH:8]=1.[CH3:36]O>C(Cl)Cl>[Cl:6][C:7]1[N:12]=[CH:11][C:10]2[C:1]([C:2]([O:4][CH3:36])=[O:3])=[N:14][N:15]([C:16]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:9]=2[CH:8]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A suspension of NaOAc (1.415 g, 17.25 mmol), Pd(dppf)C12 (0.841 g, 1.150 mmol) and 6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridine (6 g, 11.50 mmol) in MeOH (30 ml) was stirred under CO (120 psi) at 65° C. for 3 days. After reaction, the reaction mixture was diluted with DCM and dry loaded on silica column and purified by column chromatography on silica gel 120 g, eluting with 1:3 EA in Hexane to give the desired product as an off white solid 4.74 g (91% yield). MS ESI calc'd. for C27H20ClN3O2 [M+1]+ 454, found 454.

Workup

customAfter reaction
customdry
custompurified by column chromatography on silica gel 120 g
washeluting with 1:3 EA in Hexane

Sources & evidence

ORD record: ord-b7d31c59d4454c9c9ffb0683b980ba5e
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023865B2

Reaction notes

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