Triethylamine → 5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)-ethynyl]nicotinic acid

HRID 391578

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[N:16]([CH3:17])[N:15]=[C:14]([CH3:18])[CH:13]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[CH:2].Br[C:20]1[CH:21]=[N:22][CH:23]=[C:24]([CH:28]=1)[C:25]([OH:27])=[O:26].CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:17][N:16]1[C:12]([C:10]([NH:9][C:5]2[CH:4]=[C:3]([C:1]#[C:2][C:20]3[CH:21]=[N:22][CH:23]=[C:24]([CH:28]=3)[C:25]([OH:27])=[O:26])[CH:8]=[CH:7][CH:6]=2)=[O:11])=[CH:13][C:14]([CH3:18])=[N:15]1

Participants

Conditions

Temperature: 50 °C

Procedure

In a 50 mL round bottom flask, N-(3-ethynylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide (0.888 g, 3.71 mmol) and 5-bromo nicotinic acid (0.50 g, 2.47 mmol) were dissolved in DMF (15 mL) The mixture was then degassed by bubbling N2(g) through it for ˜20 min. The mixture was then treated sequentially with NEt3 (1.37 mL, 9.90 mmol), Pd(PPh3)2Cl2 (0.173 g, 0.247 mmol) and CuI (0.094 g, 4.95 mmol). The reaction mixture was allowed to stir at 50° C. for 4 h. The reaction mixture was diluted with EtOAc (25 mL) causing a pale yellow precipitate to form. The white precipitate was filtered off giving the title compound (0.105 g, 12%).

Workup

customwas then degassed
customby bubbling N2(g) through it for ˜20 min
customto form
filtrationThe white precipitate was filtered off

Sources & evidence

ORD record: ord-5388f87ef62540f18dbad60e1ebbed8b
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383825B2

Linked notes

Loading…