Sodium Carbonate → N-(4-(3,3'-bipyridin-2-yloxy)phenyl)-1-methyl-1H-benzo[d]imidazol-2-amine

HRID 410198Notes

Reaction equation

Br[C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[N:20]([CH3:21])[C:19]4[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=4[N:17]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28](B(O)O)[CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:28]2[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=2)[C:3]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:20]([CH3:21])[C:19]3[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=3[N:17]=2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a microwave vial was added N-(4-(3-bromopyridin-2-yloxy)phenyl)-1-methyl-1H-benzo[d]imidazol-2-amine (0.2082 g, 0.527 mmol), pyridin-3-ylboronic acid (0.194 g, 1.580 mmol), PdCl2(PPh2iPr2)2 (0.020 g, 0.032 mmol), and sodium carbonate (0.279 g, 2.63 mmol) in DME (1.317 mL) and Water (0.439 mL). The reaction mixture was stirred and heated in a Discover® model microwave reactor (CEM, Matthews, N.C.) at 100° C. for 15 min (60 watts, Powermax feature on, ramp time 5 min). The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (40 g), eluting with a gradient of 1% to 5% MeOH in DCM, to provide N-(4-(3,3′-bipyridin-2-yloxy)phenyl)-1-methyl-1H-benzo[d]imidazol-2-amine. MS (ESI, pos. ion) m/z: 394.0 (M+1). IC50 (uM) +++++.

Workup

customchromatographed through a Redi-Sep® pre-packed silica gel column (40 g)
washeluting with a gradient of 1% to 5% MeOH in DCM

Sources & evidence

ORD record: ord-4b9c2efbcb7b4308bc59c6fdb304fc9c
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759532B2

Reaction notes

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