2-Methoxyaniline → 6-chloro-3-methoxy-N-(2-methoxyphenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-amine

HRID 588149Notes

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][C:35]1[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=1[NH2:37].CC(C)([O-])C.[K+]>C1COCC1>[Cl:32][C:4]1[N:3]=[C:2]([NH:37][C:36]2[CH:38]=[CH:39][CH:40]=[CH:41][C:35]=2[O:34][CH3:33])[C:7]2[C:8]([O:30][CH3:31])=[N:9][N:10]([C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:6]=2[CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

4,6-dichloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine (Intermediate 37B, 100 mg, 0.217 mmol), 2-methoxyaniline (26.0 μl, 0.217 mmol), t-butyl X-Phos palladacycle (5.97 mg, 8.69 μmol) were combined in a 5 ml microwave vial. The vial was evacuated and backfilled (3×) with N2 gas before adding THF (2.2 ml) and potassium t-butoxide (326 μl, 0.326 mmol). The reaction was allowed to stir at 80° C. for 2 hours. Room temperature was attained and the mixture was filtered through a celite frit and concentrated in vacuo while loading onto silica gel. Purifcation by MPLC 0-20% EtOAc/DCM gave 6-chloro-3-methoxy-N-(2-methoxyphenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-amine (52B). MS: [M+H]+ m/z 547.

Workup

customThe vial was evacuated
customRoom temperature
filtrationthe mixture was filtered through a celite frit
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6329add573864d84849cbb603804ec8a
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

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