Diisopropylethylamine → 3-Bromo-6-trityl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine

HRID 225521

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH2:10]Br)[C:5]([CH2:8]Br)=[N:6][CH:7]=1.[C:12]([NH2:31])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:10][N:31]([C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:8][C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 0.87 mmol 5-Bromo-2,3-bis-bromomethyl-pyridine, 1.1 mmol tritylamine, and 2.61 mmol DIPEA in 3 ml DMF was stirred at 60° C. for 2 h. The reaction mixture was evaporated in vacuo. The residue was taken in water and extracted with ethylacetate. The combined organic phases were washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/dichloromethane) to yield the title compound as a light brown solid. MS (m/e): 243.4 (tritylion, 100%)

Workup

customThe reaction mixture was evaporated in vacuo
extractionextracted with ethylacetate
washThe combined organic phases were washed with water
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by chromatography (SiO2, heptane/dichloromethane)

Sources & evidence

ORD record: ord-a137a8f9ca30484f9ca5f82197ed84d8
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557114B2

Linked notes

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