Potassium Carbonate → HCID 58102999, compound

HRID 1040245Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[N:21]([CH:22]4[CH2:24][CH2:23]4)[CH:20]=[N:19][N:18]=3)[CH:12]=2)=[O:9])[CH:3]=1.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27](B(O)O)[CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH:22]1([N:21]2[CH:20]=[N:19][N:18]=[C:17]2[C:13]2[CH:12]=[C:11]([NH:10][C:8]([C:4]3[CH:3]=[C:2]([C:27]4[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=4)[CH:7]=[CH:6][N:5]=3)=[O:9])[CH:16]=[CH:15][CH:14]=2)[CH2:24][CH2:23]1

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 4-bromo-N-(3-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)phenyl)picolinamide (120 mg, 0.31 mmol), 3-pyridine boronic acid (77 mg, 0.62 mmol), dppf(Pd)Cl2 (23 mg, 0.03 mmol), potassium carbonate (86 mg, 0.62 mmol) in degassed toluene (2 mL), degassed water (1 mL) and degassed ethanol (1 mL) was heated at 100° C. for 1 hour. The solvent was removed under reduced pressure and the residue purified by reverse-phase HPLC, to give N-(3-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)phenyl)-3,4′-bipyridine-2′-carboxamide as a white powder (58 mg, 0.15 mmol, 48% yield). C22H18N6O. 383.1 (M+1). 1H NMR (DMSO) d 10.98 (s, 1H), 9.12 (d, J=1.6 Hz, 1H), 8.87 (d, J=4.8 Hz, 1H), 8.72 (dd, J=4.8, 1.2 Hz, 1H), 8.63 (s, 1H), 8.60 (s, 1H), 8.48 (d, J=1.2 Hz, 1H), 8.34 (m, 1H), 8.11 (m, 2H), 7.69 (d, J=8.0 Hz, 1H), 7.59 (m, 2H), 3.66 (m, 1H), 1.09 (m, 2H), 0.94 (m, 2H).

Workup

customdegassed water (1 mL)
customdegassed ethanol (1 mL)
customThe solvent was removed under reduced pressure
customthe residue purified by reverse-phase HPLC

Sources & evidence

ORD record: ord-f088de92896c46118348f47f47a2a44a
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552196B2

Reaction notes

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