Iodine → 7-Benzyl-5-iodo-3-methyl-7,9-dihydro-dipyrido[2,3-b; 4',3'-d]pyrrol-8-one

HRID 1882204Notes

Reaction equation

[CH2:1]([N:8]1[CH:21]=[C:20]([Si](C)(C)C)[C:11]2[C:12]3[CH:18]=[C:17]([CH3:19])[CH:16]=[N:15][C:13]=3[NH:14][C:10]=2[C:9]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:27]I>C(O)C.F[B-](F)(F)F.[Ag+]>[CH2:1]([N:8]1[CH:21]=[C:20]([I:27])[C:11]2[C:12]3[CH:18]=[C:17]([CH3:19])[CH:16]=[N:15][C:13]=3[NH:14][C:10]=2[C:9]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Compound 28 (2.5 g, 6.93 mmol) dissolved in dry ethanol (200 mL) and stirred under nitrogen at 0° C. Silver tetrafluoroborate (1.45 g, 7.45 mmol) was added, and the solution stirred for 10 minutes. Iodine (1.85 g, 7.3 mmol) was added, and the reaction stirred 1 h as a precipitate began to form. After evaporation of the solvent, the solid was taken up in CH2Cl2 and washed with water, which caused an insoluble precipitate to form. The solid was collected by filtration and washed with ethyl acetate to leave 2.5 g (87%) of intended product. 1H NMR (400 MHz, DMSO-d6): δ 12.74 (s, 1H), 8.69 (s, 1H), 8.42 (s, 1H), 7.90 (s, 1H), 7.25-7.36 (m, 5H), 5.26 (s, 2H), 2.46 (s, 3H). MS (ES) [m+H] calc'd for C18H14IN3O, 416; found 416.

Workup

stirringthe solution stirred for 10 minutes
stirringthe reaction stirred 1 h as a precipitate
customto form
customAfter evaporation of the solvent
washwashed with water, which
customto form
filtrationThe solid was collected by filtration
washwashed with ethyl acetate

Sources & evidence

ORD record: ord-69ecca7c36a744fda9c1a13cc843a675
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318939B2

Reaction notes

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