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Sodium Carbonate → Methyl 4'-[3-[(trifluoroacetyl)amino]propyl]-1,1'-biphenyl-4-carboxylate

HRID 1823094
Notes
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Reaction equation

HRID 1823094 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12](I)=[CH:11][CH:10]=1)=[O:4].[CH3:18][O:19][C:20]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)=[O:21].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.O.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>[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:25]2[CH:26]=[CH:27][C:22]([C:20]([O:19][CH3:18])=[O:21])=[CH:23][CH:24]=2)=[CH:11][CH:10]=1)=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 221714282,2,2-trifluoro-N-[3-(4-iodophenyl)-propyl]acetamide

Product 1

HCID 22171344Methyl 4'-[3-[(trifluoroacetyl)amino]propyl]-1,1'-biphenyl-4-carboxylateYield 36%

Reagents, catalysts & solvents 4

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent
HCID 80711,2-DimethoxyethaneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 2,2,2-trifluoro-N-[3-(4-iodophenyl)propyl]acetamide (2.5 g) in 1,2-dimethoxyethane (15 ml) was added [4-(methoxycarbonyl)phenyl]boronic acid (1.51 g), tetrakis(triphenylphosphine)palladium (809 mg) and aqueous solution of sodium carbonate (2M, 7 ml), and the mixture was stirred at 75° C. for 10 hours under nitrogen. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to give methyl 4′-[3-[(trifluoroacetyl)amino]propyl]-1,1′-biphenyl-4-carboxylate (920 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-4d12b17196154f4a9cd3ceb19ba18396
Source dataset
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07037938B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes