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

HRID 576645Notes

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.C(N(C(C)C)CC)(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

To a solution of 5-bromo-2,3-bis(bromomethyl)pyridine (Step 2 above, 5.6 g, approximately 16.3 mmol) in DMF (40 mL) was added trityl amine (5.3 g, 20.6 mmol) followed by diisopropylethylamine (8.6 mL, 49 mmol). The resulting solution was warmed to 60° C. and stirred at this temperature for 2.5 hr. The mixture was then concentrated under reduced pressure and the residue was purified by silica chromatography (50 g silica, eluted with 10-100% dichloromethane in hexanes) to give the title compound as a foam.

Workup

concentrationThe mixture was then concentrated under reduced pressure
customthe residue was purified by silica chromatography (50 g silica, eluted with 10-100% dichloromethane in hexanes)

Sources & evidence

ORD record: ord-b357b59c7c5f42ff9eb8a3ee56489f8a
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040504B2

Reaction notes

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