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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
Notes
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Reaction equation

HRID 1521649 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-25e251c6616149829d2ab36095535b68
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09073929B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes