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Lithium Chloride → HCID 56839569, compound

HRID 537050
Notes
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Reaction equation

HRID 537050 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11](I)=[N:10][C:9]=1[C:14]([NH2:16])=[O:15].[CH3:17][C:18]1[C:19]([Sn](C)(C)C)=[CH:20][C:21]([NH:24][C:25]([CH:27]2[CH2:29][CH2:28]2)=[O:26])=[N:22][CH:23]=1.[Cl-].[Li+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11]([C:19]2[C:18]([CH3:17])=[CH:23][N:22]=[C:21]([NH:24][C:25]([CH:27]3[CH2:29][CH2:28]3)=[O:26])[CH:20]=2)=[N:10][C:9]=1[C:14]([NH2:16])=[O:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 433294Lithium ChlorideHCID 66747440HCID 66747440, compoundHCID 66749598HCID 66749598, compound

Product 1

HCID 56839569HCID 56839569, compoundYield 64.8%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst
HCID 178418397HCID 178418397, compoundCatalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(2-chlorophenyl)-2-iodo-1,3-oxazole-4-carboxamide (0.051 g, 0.14 mmol), N-[5-methyl-4-(trimethylstannyl)pyridine-2-yl]cyclopropanecarboxamide (0.064 g, 0.19 mmol), tetrakis(triphenylphosphine)palladium(0) (0.008 g, 0.007 mmol), copper(I) iodide (0.008 g, 0.043 mmol), and lithium chloride (0.018 g, 0.43 mmol) in 1,4-dioxane (1.5 mL) was degassed with argon three times and then allowed to stir at 100° C. under an atmosphere of argon for 5 h. The reaction mixture was filtered while hot and the filtrate was concentrated. The residue was purified by column chromatography to give 5-(2-chlorophenyl)-2-{2-[(cyclopropylcarbonyl)amino]-5-methylpyridin-4-yl}-1,3-oxazole-4-carboxamide (Compound I-86) (0.036 g, 62%). LCMS (AA): m/z=397 (M+H).

Workup

  1. customwas degassed with argon three times
  2. filtrationThe reaction mixture was filtered while hot and the filtrate
  3. concentrationwas concentrated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d3763c52c19d4263bd89c7a8d8f3efea
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08859768B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes