Methyl iodide → tert-butyl(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)(methyl)carbamate

HRID 588145Notes

Reaction equation

[C:1]([O:5][C:6](=[O:39])[NH:7][C:8]1[C:13]2[C:14]([O:36][CH3:37])=[N:15][N:16]([C:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([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]=2[CH:11]=[C:10]([Cl:38])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:40]([O-])([O-])=O.[Cs+].[Cs+].IC.[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:39])[N:7]([C:8]1[C:13]2[C:14]([O:36][CH3:37])=[N:15][N:16]([C:17]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)([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]=2[CH:11]=[C:10]([Cl:38])[N:9]=1)[CH3:40])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

t-Butyl(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)carbamate (45B, 86 mg, 0.159 mmol) was taken up in DMF (1.6 ml). Cs2CO3 (104 mg, 0.318 mmol) followed by iodomethane (10.93 μl, 0.175 mmol) were added. The reaction was allowed to stir at 60° C. for 2 hours. EtOAc and saturated NH4Cl were added. The products were extracted into EtOAc (3×). The combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo to give tert-butyl(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)(methyl)carbamate (46B). Reaction products were carrried forward without purification. MS: [M+H]+ m/z 555.

Workup

additionwere added
extractionThe products were extracted into EtOAc (3×)
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7d7b9ba15ec24410bd66b2a9fdd8518a
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

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