Potassium Carbonate → 6-(2-cyanophenyl)-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide

HRID 2080277Notes

Reaction equation

Cl[C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:7])=[C:4]([NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[N:3]=1.[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O)#[N:29].C([O-])([O-])=O.[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CN(C=O)C>[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:7])=[C:4]([NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[N:3]=1)#[N:29]

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 6-chloro-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide (1.0 g, 2.6 mmol), 2-cyanophenyl boronic acid (460 mg, 3.12 mmol), PdCl2(dppf)2 (140 mg, 0.26 mmol), K2CO3 (1.08 g, 7.8 mmol) and anhydrous DMF (8 mL) was degassed with nitrogen for 10 min. The mixture was then stirred at 125° C. for 1 hr. The mixture was filtered through the silica gel pad and washed with EtOAc. The filtrate was concentrated to dryness and purified by silica gel flash chromatography to give the desired product 6-(2-cyanophenyl)-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide as a pale yellow solid (740 mg, 63%). LRMS (M+H+) m/z 452.1.

Workup

customwas degassed with nitrogen for 10 min
filtrationThe mixture was filtered through the silica gel pad
washwashed with EtOAc
concentrationThe filtrate was concentrated to dryness
custompurified by silica gel flash chromatography

Sources & evidence

ORD record: ord-339097cbfef74fedbf0c74ae62706d76
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932270B2

Reaction notes

Loading…