Sodium Methoxide → 6-chloro-3,4-dimethoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine

HRID 588155Notes

Reaction equation

Cl[C:2]1[C:7]2[C:8]([O:30][CH3:31])=[N:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[CH:5]=[C:4]([Cl:32])[N:3]=1.[CH3:33][O-:34].[Na+]>C1COCC1.C(Cl)Cl>[Cl:32][C:4]1[N:3]=[C:2]([O:34][CH3:33])[C:7]2[C:8]([O:30][CH3:31])=[N:9][N:10]([C:11]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:6]=2[CH:5]=1

Participants

Conditions

Temperature: 40 °C

Procedure

4,6-dichloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine (Intermediate 37B, 100 mg, 0.217 mmol) in THF (1086 μl) was treated with sodium methoxide (4.6 N in MeOH) (51.9 μl, 0.239 mmol) and stirred @ 40° C. for 1 h. Reaction was diluted in with DCM and concentrated in vacuo on silica. Material was purified by normal phase column chromotography eluting with Hex/EtOAc (0-10%) affording 6-chloro-3,4-dimethoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine (56B, 86 mg, 0.189 mmol, 87% yield) as a white foam. MS: [M+H]+ m/z 456.

Workup

customReaction
concentrationconcentrated in vacuo on silica
customMaterial was purified by normal phase column chromotography
washeluting with Hex/EtOAc (0-10%)

Sources & evidence

ORD record: ord-cca61eb22b2441f0afbffb37da64334a
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

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