Trityl chloride → HCID 89525914, compound

HRID 588094Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[C:8]2[CH:9]=[N:10][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:12][C:7]=2[NH:6][N:5]=1.[C:17]1([C:23](Cl)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[Br:3][C:4]1[C:8]2[CH:9]=[N:10][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:12][C:7]=2[N:6]([C:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

At 0° C., NaH (60% in mineral oil, 1.172 g, 29.3 mmol) was added in portions to a suspension of methyl 3-bromo-1H-pyrazolo[4,3-c]pyridine-6-carboxylate (5.0 g, 19.53 mmol) in DMF (50 mL). The reaction mixture was stirred at 0° C. for 30 min, then a solution of triphenylmethyl chloride (6.53 g, 23.43 mmol) in DMF (50 mL) was added drop-wise. The reaction mixture was slowly warmed to room temperature overnight, quenched with H2O, and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (20% EtOAc/hexanes) to give methyl 3-bromo-1-trityl-1H-pyrazolo[4,3-c]pyridine-6-carboxylate. MS ESI calc'd. for C27H21BrN3O2 [M+H]+ 498. found 498.

Workup

temperatureThe reaction mixture was slowly warmed to room temperature overnight
customquenched with H2O
extractionextracted with EtOAc
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record: ord-ad2b92669f8944789593c042a71f3db5
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

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