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Sodium Carbonate → 6-Chloro-7-(5-fluoropyridin-3-yl)-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

HRID 1521649
ノート
印刷プレビュー

反応式

HRID 1521649 の反応式
Br[C:2]1[C:3]([Cl:16])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:12]([CH3:15])=[N:13][N:14]=[C:7]1[CH2:6][CH2:5]2.[F:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[N:22][CH:23]=1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>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].O>[Cl:16][C:3]1[C:2]([C:20]2[CH:21]=[N:22][CH:23]=[C:18]([F:17])[CH:19]=2)=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7]1[N:8]2[C:12]([CH3:15])=[N:13][N:14]=1
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 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 709781657-Bromo-6-chloro-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

生成物 1

HCID 899617716-Chloro-7-(5-fluoropyridin-3-yl)-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

試薬・触媒・溶媒 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of 7-bromo-6-chloro-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline (143-7; 0.20 g, 0.0006 mol) and (5-fluoropyridin-3-yl)boronic acid (0.93 g, 0.0006 mol) in the mixture of 1,4-dioxan (10 mL) and water (10 mL) was added sodium carbonate (0.127 g, 0.0012 mol). Reaction mass was purged with argon for 20 min. Then catalyst Pd(dppf)2Cl2 (0.048 g, 0.00006 mol) was added and allowed to stir at 80° C. for 12 h. The reaction mixture was filtered through CELITE bed and filter bed was thoroughly washed with ethyl acetate. The collected organic part was concentrated under vacuum to afford the crude compound, which was purified by silica gel column chromatography to obtain title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.659-8.652 (d, J=2.8 Hz, 1H), 8.514 (s, 1H), 7.908-7.884 (d, J=9.6 Hz, 1H), 7.789-7.768 (d, J=8.4 Hz, 1H), 7.566-7.504 (d, J 8.4 Hz, 1H), 3.186-3.152 (m, 2H), 3.084-3.035 (m, 2H), 2.695 (s, 3H). MS (M+1): 315.1.

後処理

  1. customReaction mass
  2. customwas purged with argon for 20 min
  3. filtrationThe reaction mixture was filtered through CELITE bed
  4. filtrationfilter bed
  5. washwas thoroughly washed with ethyl acetate
  6. concentrationThe collected organic part was concentrated under vacuum
  7. customto afford the crude compound, which
  8. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-25e251c6616149829d2ab36095535b68
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09073929B2

反応ノート

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