Potassium Carbonate → HCID 67341091, compound

HRID 1846655Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([NH:25][C:26](=[O:34])[C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=2)[C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([N:17]3[CH2:23][CH2:22][CH2:21][N:20]([CH3:24])[CH2:19][CH2:18]3)=[O:16])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[N:35]1[CH:40]=[CH:39][CH:38]=[C:37](B(O)O)[CH:36]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)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>[Cl:33][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][CH:30]=1)[C:26]([NH:25][C:4]1[C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([N:17]3[CH2:23][CH2:22][CH2:21][N:20]([CH3:24])[CH2:19][CH2:18]3)=[O:16])[CH2:10][CH2:9]2)=[N:6][CH:7]=[C:2]([C:37]2[CH:36]=[N:35][CH:40]=[CH:39][CH:38]=2)[CH:3]=1)=[O:34]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 0.050 g (0.091 mmol) of N-{5′-bromo-4-[2-(4-methyl-[1,4]diazepan-1-yl)-2-oxo-ethyl]-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-yl}-3-chloro-benzamide in N,N-dimethylformamide (3 mL) is added 0.011 g (0.091 mmol) of 3-pyridyl boronic acid followed by 0.100 g (0.725 mmol) of potassium carbonate and 0.010 g (0.009 mmol) of tetrakis(triphenylphosphine)palladium(0). The mixture is flushed with argon for 2 minutes and heated at 80° C. for 18 hours. The mixture is filtered and purified by preparative reverse phase HPLC to provide 0.007 g (14%) of the title compound (125) as a white solid. [M+H]+=547.8.

Workup

customThe mixture is flushed with argon for 2 minutes
filtrationThe mixture is filtered
custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record: ord-00b2bd328d9d426d9963ce02b8cf189d
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952004B2

Reaction notes

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