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Methanol → HCID 68194235, compound

HRID 1520156
Notes
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Reaction equation

HRID 1520156 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[C:13]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[N:14][C:15]3[C:20]([N:21]=1)=[CH:19][C:18]([C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=3)[CH2:7][CH2:6][CH2:5]2.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.[CH3:39][OH:40]>O1CCOCC1.ClCCl.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]>[F:32][C:29]1[CH:28]=[CH:27][C:26]([C:13]2[C:12]([N:8]3[C:9]4[C:4](=[CH:3][C:2]([C:39]([N:33]5[CH2:38][CH2:37][O:36][CH2:35][CH2:34]5)=[O:40])=[CH:11][CH:10]=4)[CH2:5][CH2:6][CH2:7]3)=[N:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=3)[N:14]=2)=[CH:31][CH:30]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 887MethanolHCID 8083MorpholineHCID 68194082HCID 68194082, compound

Product 1

HCID 68194235HCID 68194235, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst
HCID 6344DichloromethaneSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 3-(6-bromo-1,2,3,4-tetrahydroquinolin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylate (130 mg, 0.26 mmol) in dioxane (25 ml) was added morpholine (35 mg, 0.40 mmol) and Pd(dppf)2Cl2 (6.7 mg, 0.05 mmol) with stirring overnight maintained with atmosphere of CO (g) at 100° C. under 5 Atm. The reaction mixture was concentrated under vacuum to give a residue, which was applied onto a silica gel column with 1% methanol in dichloromethane to afford methyl 2-(4-fluorophenyl)-3-[6-[(morpholin-4-yl)carbonyl]-1,2,3,4-tetrahydroquinolin-1-yl]quinoxaline-6-carboxylate as a yellow solid (107 mg, 77%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customto give a residue, which

Sources & evidence

ORD record
ord-35dd27719c3c44a68fff48c02f97f197
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09073902B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes