Phenylboronic Acid → [4-(1H-benzimidazol-2-yl)piperidin-1-yl](5-phenylpyridin-2-yl)methanone

HRID 1913151Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([C:18]2[CH:23]=[CH:22][C:21](Br)=[CH:20][N:19]=2)=[O:17])[CH2:12][CH2:11]1.[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])(O)=O.[Na+]>CO.O1CCOCC1>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:20][N:19]=2)=[O:17])[CH2:12][CH2:11]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred mixture of [4-(1H-benzimidazol-2-yl)piperidin-1-yl](5-bromopyridin-2-yl)methanone (39 mg, 0.10 mmol) and phenylboronic acid (20.1 mg, 0.17 mmol) in a mixture of MeOH (0.5 mL) and 1,4-dioxane (1.5 mL) is added 2M aqueous NaHCO3 (0.3 mL). The mixture is degassed with N2. 1,1′-bis(diphenylphosphino)ferrocene-palladium (II) dichloride dichloromethane complex (5 mol %) is added and the mixture is heated at 100° C. under microwave irradiation for 30 mins. The mixture is filtered through a pad of celite and the filtrate is concentrated under reduced pressure. Purification by column chromatography (Isolute column, eluent DCM, 5% MeOH) affords 30.6 mg of [4-(1H-benzimidazol-2-yl)piperidin-1-yl](5-phenylpyridin-2-yl)methanone.

Workup

customThe mixture is degassed with N2
addition1,1′-bis(diphenylphosphino)ferrocene-palladium (II) dichloride dichloromethane complex (5 mol %) is added
filtrationThe mixture is filtered through a pad of celite
concentrationthe filtrate is concentrated under reduced pressure
customPurification by column chromatography (Isolute column, eluent DCM, 5% MeOH)

Sources & evidence

ORD record: ord-be55d9af120f422ebe5af677fd8409b2
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609696B2

Reaction notes

Loading…