4-Iodo-2-methoxynicotinaldehyde → {1-[2-(4-Iodo-2-methoxy-pyridin-3-yl)-7-methyl-3H-benzoimidazol-5-yl]-piperidin-4-yl}-carbamic acid tert-butyl ester

HRID 1354630Notes

Reaction equation

[C:1]([O:5][C:6](=[O:25])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([CH3:20])[C:17]([N+:21]([O-])=O)=[C:16]([NH2:24])[CH:15]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H][H].[I:28][C:29]1[CH:34]=[CH:33][N:32]=[C:31]([O:35][CH3:36])[C:30]=1[CH:37]=O>CO.[Pd]>[C:1]([O:5][C:6](=[O:25])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([CH3:20])[C:17]3[N:21]=[C:37]([C:30]4[C:31]([O:35][CH3:36])=[N:32][CH:33]=[CH:34][C:29]=4[I:28])[NH:24][C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

[1-(3-Amino-5-methyl-4-nitro-phenyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (1.54 g, 4.4 mmol) was dissolved in methanol (100 ml). Palladium on carbon (0.3 g, 10% Pd) was added and the suspension stirred vigorously under a balloon pressure of hydrogen overnight. The mixture was filtered through a pad of celite (under argon) into a 3-neck flask, the celite rinsed with methanol and the filtrate cooled to 0° C. A solution of 4-Iodo-2-methoxy-pyridine-3-carbaldehyde (1.21 g, 4.6 mmol) in methanol (50 ml) was added slowly (during 2 hours). The mixture was stirred overnight under air at ambient temperature, then concentrated in vacuo. Flash column chromatography on silica (eluent hexanes-ethyl acetate-methanol 5-4-1 gave the title compound. (0.79 g, 32%). LCMS (M+H)+ m/z 564 (t=1.31 min.).

Workup

filtrationThe mixture was filtered through a pad of celite (under argon) into a 3-neck flask
washthe celite rinsed with methanol
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-694fb80327c9472899f5b7a0301f4473
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223757B2

Reaction notes

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