Potassium Carbonate → (E)-2-(3-fluorophenethylamino)-6-(prop-1-enyl)-N-(pyridin-3-ylmethyl)nicotinamide

HRID 547503Notes

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.[Cl-].[CH:29](/B(O)O)=[CH:30]\[CH3:31].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].C1COCC1>[F:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:20][CH2:19][NH:18][C:4]1[N:3]=[C:2](/[CH:29]=[CH:30]/[CH3:31])[CH:17]=[CH:16][C:5]=1[C:6]([NH:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:7]

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of chloride 6-chloro-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide (100 mg, 0.260 mmol), trans-1-propen-1-yl boronic acid (27 mg, 0.312 mmol), PdCl2(dppf)2 (14 mg, 0.026 mmol), 2N K2CO3(0.39 mL, 0.78 mmol) and THF (1.5 mL) was stirred at 125° C. for 30 min. The mixture was filtered through the silica gel pad and washed with EtOAc. The filtrate was concentrated to dryness and purified on RP-HPLC using a mixture of acetonitrile and H2O to give (E)-2-(3-fluorophenethylamino)-6-(prop-1-enyl)-N-(pyridin-3-ylmethyl)nicotinamide as a pale yellow solid (59 mg, 86%). LRMS (M+H+) m/z 391.2.

Workup

filtrationThe mixture was filtered through the silica gel pad
washwashed with EtOAc
concentrationThe filtrate was concentrated to dryness
custompurified on RP-HPLC
additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record: ord-1fd1104ffdf440eebb2b026c19def4aa
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07939548B2

Reaction notes

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