Iodoethane → HCID 86699768, compound

HRID 515205Notes

Reaction equation

[Br:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)=[O:7])=[CH:4][CH:3]=1.C(O)(=O)[C:22]([CH3:25])(C)C.C(=O)([O-])[O-].[K+].[K+].[CH2:34](I)[CH3:35]>C(O)(CC)(C)C.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:20]=[C:19]([CH2:34][CH3:35])[C:5]([C:6]([NH:8][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)=[O:7])=[C:4]([CH2:22][CH3:25])[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-bromo-N-quinolin-8-yl-benzamide (3.2 g, 9.79 mmol) in tert-amyl alcohol (10 ml) are added pivalic acid (0.2 g, 1.96 mmol), potassium carbonate (3.37 g, 24.5 mmol) and ethyl iodide (6.36 ml, 78.3 mmol) in a sealed tube. After degassing with argon for 30 min palladium(II) acetate (0.11 g, 0.49 mmol) is added and the mixture is heated at 100° C. for 48 h. After completion of the reaction (monitored by TLC) the mixture is diluted with ethyl acetate (50 ml), washed with water (2×30 ml), and the organic layer is dried over sodium sulfate and concentrated in vacuo. The resulting crude product is purified by column chromatography (silica gel, 10% ethyl acetate/hexane) to yield 4-bromo-2,6-diethyl-N-quinolin-8-yl-benzamide (2.9 g, 7.57 mmol, 77%).

Workup

additionis added
customAfter completion of the reaction (monitored by TLC) the mixture
washwashed with water (2×30 ml)
dry with materialthe organic layer is dried over sodium sulfate
concentrationconcentrated in vacuo
customThe resulting crude product is purified by column chromatography (silica gel, 10% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-248097fda0694034951e3c6e392669a9
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108936B2

Reaction notes

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