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Dimethylformamide → Methyl 6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinate

HRID 2080273
Notes
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Reaction equation

HRID 2080273 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[N:3]=1.[Cl-].[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O)#[N:24].C([O-])([O-])=O.[K+].[K+].[CH3:40][N:41]([CH:43]=O)C>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]>[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:3][CH2:2][C:11]2[CH:40]=[N:41][CH:43]=[CH:5][CH:10]=2)=[O:8])=[C:4]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[N:3]=1)#[N:24].[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[N:3]=1)#[N:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27346102-Cyanophenylboronic acidHCID 86626130Chloride methyl 6-chloro-2-(3-fluorophenethylamino)nicotinate

Product 2

HCID 57542380Methyl 6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinateYield 82%
HCID 57542525
6-(2-cyanophenyl)-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide

Reagents, catalysts & solvents 1

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
100 °C

Procedure

A mixture of chloride methyl 6-chloro-2-(3-fluorophenethylamino)nicotinate (30.8 g, 0.1 mol), 2-cyanophenyl boronic acid (17.6 g, 0.12 mol), PdCl2(dppf)2 (3.6 g, 5.0 mmol), K2CO3 (41.4 g, 0.3 mol) and anhydrous DMF (100 mL) was degassed with nitrogen for 30 min. The mixture was then stirred at 100° C. for 2 hrs. The mixture was filtered through the Celite and washed with EtOAc. The filtrate was diluted with EtOAc, washed with brine and concentrated to dryness. The residue was purified by silica gel flash chromatography using hexane-EtOAc (4:1) as eluant to give the desired product methyl 6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinate as a yellow solid (31 g, 82%). LRMS (M+H+) m/z 376.1.

Workup

  1. customwas degassed with nitrogen for 30 min
  2. filtrationThe mixture was filtered through the Celite
  3. washwashed with EtOAc
  4. additionThe filtrate was diluted with EtOAc
  5. washwashed with brine
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-f5e187d44544445d97e35997c9398d3e
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07932270B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes