(2-Methoxypyridin-4-yl)boronic acid → 4-[5-(2-Methoxy-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino]-N-pyridin-3-ylmethyl-benzamide

HRID 1011272Notes

Reaction equation

Cl[C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:11][C:12]2[CH:27]=[CH:26][C:15]([C:16]([NH:18][CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[O:17])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[CH3:28][O:29][C:30]1[CH:35]=[C:34](B(O)O)[CH:33]=[CH:32][N:31]=1.CC([O-])(C)C.[Na+]>CN(C=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:28][O:29][C:30]1[CH:35]=[C:34]([C:2]2[N:7]3[N:8]=[CH:9][N:10]=[C:6]3[C:5]([NH:11][C:12]3[CH:27]=[CH:26][C:15]([C:16]([NH:18][CH2:19][C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)=[O:17])=[CH:14][CH:13]=3)=[CH:4][CH:3]=2)[CH:33]=[CH:32][N:31]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A suspension of 4-(5-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-N-pyridin-3-ylmethyl-benzamide (50 mg, 132 μmol), 2-methoxypyridin-4-boronic acid (40 mg, 260 μmol), Pd(PPh3)4 (46 mg, 40 μmol) and NaOtBu (51 mg, 530 μmol) in 1.2 mL of DMF/water (5:1, degassed) is degassed for 1 min in a sealed tube. The tube is sealed and the reaction mixture heated at 110° C. for five hours. After evaporation of the solvents, the residue is purified by flash chromatography (silica gel, dichloromethane/7N NH3 in methanol 97:3) affording the title compound (46 mg), which is isolated as a mixture containing 50% of product.

Workup

customis degassed for 1 min in a sealed tube
customThe tube is sealed
customAfter evaporation of the solvents
customthe residue is purified by flash chromatography (silica gel, dichloromethane/7N NH3 in methanol 97:3)

Sources & evidence

ORD record: ord-1388e9b8615e4041b01117aaebe01e15
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977352B2

Reaction notes

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