Morpholine → 2-(1-methylethyl)-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-4-nitro-1H-benzimidazole

HRID 1188784Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([N+:25]([O-:27])=[O:26])[C:5]2[N:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[N:7]([CH2:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:24]=1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.C([O-])([O-])=O.[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:11][CH:10]([C:8]1[N:7]([CH2:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[C:6]2[CH:24]=[C:2]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[CH:3]=[C:4]([N+:25]([O-:27])=[O:26])[C:5]=2[N:9]=1)[CH3:12]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-bromo-2-(1-methylethyl)-1-(1-naphthalenylmethyl)-4-nitro-1H-benzimidazole (2.05 g), morpholine (1.26 g), Pd2(dba)3 (0.46 g), Cs2CO3 (2.36 g) and X-Phos (0.41 g) in dioxane (30 mL) was degassed with nitrogen and then stirred at 80° C. overnight. The mixture was cooled to room temperature and the solvent was removed in-vacuo. The residue was then purified by silica gel chromatography eluted with (EtOAc:petroleum ether=1:1) to afford the desired product as a yellow solid (1.6 g, 77%). LC-MS: m/e=431 [M+1]+

Workup

customwas degassed with nitrogen
temperatureThe mixture was cooled to room temperature
customthe solvent was removed in-vacuo
customThe residue was then purified by silica gel chromatography
washeluted with (EtOAc:petroleum ether=1:1)

Sources & evidence

ORD record: ord-7009681d3ba541b6a304ad9fed59a871
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674090B2

Reaction notes

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