Sodium Carbonate → 3-{5-[(2-Cyclohexylethylamino)methyl]pyridin-2-yl}-4-methylbenzamide

HRID 561363Notes

Reaction equation

[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1B1OC(C)(C)C(C)(C)O1.Br[C:21]1[N:26]=[CH:25][C:24]([CH2:27][NH:28][CH2:29][CH2:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:23][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[CH:31]1([CH2:30][CH2:29][NH:28][CH2:27][C:24]2[CH:23]=[CH:22][C:21]([C:3]3[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=3[CH3:1])[C:6]([NH2:8])=[O:7])=[N:26][CH:25]=2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzamide (Preparation 18, 150 mg, 0.57 mmol) and (6-bromopyridin-3-ylmethyl)-(2-cyclohexylethyl)amine (Preparation 15, 188 mg, 0.63 mmol) in dioxane (3 mL) was added 2M Na2CO3 (1 mL) and bis(diphenylphosphinoferrocene)-palladium dichloride (47 mg, 0.06 mmol). The mixture was purged with argon for 10 min and the mixture heated to 70° C. for 6 h. On cooling to rt, EtOAc (50 mL) was added and the organic phase washed with water (2×30 mL), brine (30 mL) and dried (MgSO4). The solvent was removed in vacuo and the residue purified by column chromatography (0.4% NH3: 4% MeOH: DCM) to give the title compound: RT=2.53 min; m/z (ES+)=352.2 [M+H]+.

Workup

customThe mixture was purged with argon for 10 min
temperatureOn cooling to rt
additionEtOAc (50 mL) was added
washthe organic phase washed with water (2×30 mL), brine (30 mL)
dry with materialdried (MgSO4)
customThe solvent was removed in vacuo
customthe residue purified by column chromatography (0.4% NH3: 4% MeOH: DCM)

Sources & evidence

ORD record: ord-1139a2372dcb4f238ead804bfaa08240
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063247B2

Reaction notes

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