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Ethanethiol → HCID 67423809, compound

HRID 230862
Notes
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Reaction equation

HRID 230862 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([NH:14]C(=O)OC(C)(C)C)=[O:13])=[C:5]2[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1.CC(C)([O-])C.[K+].[CH2:37]([SH:39])[CH3:38]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].O(C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:37]([S:39][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([NH2:14])=[O:13])=[C:5]2[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1)[CH3:38]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 6343EthanethiolHCID 23665647Potassium tert-butoxideHCID 57763225HCID 57763225, compound

Product 1

HCID 67423809HCID 67423809, compound

Reagents, catalysts & solvents 3

HCID 4285986Bis[2-(diphenylphosphino)phenyl] etherCatalyst
HCID 6505921
(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Intermediate 37 (0.100 g) was combined with (oxydi-2,1-phenylene)bis(diphenylphosphine) (0.011 g), potassium tert-butoxide (0.025 g) and tris(dibenzylideneacetone)dipalladium(o) (0.008 g) in 1,4-dioxane (1 ml). Ethanethiol (available from Aldrich, 0.023 ml) was added and the mixture was stirred under microwave irradiation (power 40 W) for 8 min at 90° C. The reaction was quenched by addition of 4M HCl in dioxane, then partitioned between ethyl acetate and sodium bicarbonate solution. The organic layer was concentrated in vacuo to give 0.090 g of crude 6-(ethylthio)-4-{[3-(methyloxy)phenyl]amino}-3-quinolinecarboxamide.

Workup

  1. customThe reaction was quenched by addition of 4M HCl in dioxane
  2. custompartitioned between ethyl acetate and sodium bicarbonate solution
  3. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-4ad3683da0d04db8af842e18ed26ee18
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07566786B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes