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

HRID 2080273
ノート
印刷プレビュー

反応式

HRID 2080273 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 2

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

試薬・触媒・溶媒 1

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

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f5e187d44544445d97e35997c9398d3e
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07932270B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート