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Furan-3-boronic acid → HCID 22631052, compound

HRID 2416551
Notes
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Reaction equation

HRID 2416551 reaction equation
[O:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.Br[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:12][CH:11]=1>C(O)C.COCCOC.C(OCC)(=O)C.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>[O:1]1[CH:5]=[CH:4][C:3]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[N:17]=[CH:18][CH:19]=[CH:20][N:21]=3)=[CH:12][CH:11]=2)=[CH:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 2734358Furan-3-boronic acidHCID 222875442-(4-Bromophenyl)pyrimidine

Product 1

HCID 22631052HCID 22631052, compoundYield 65%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent
HCID 8071
1,2-Dimethoxyethane
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 3-furanboronic acid (672 mg, 6 mmol) in 2M aq. Na3CO3 (10 mL, 20 mmol) and ethanol (8 mL) was added to a solution of 2-(4-bromo-phenyl)pyrimidine (1.30 g, 5.55 mmol, prepared as described in U.S. Pat. No. 5,780,473) and tetrakis(triphenylphosphine)palladium (693 mg, 0.60 mmol) in DME (30 mL). The reaction mixture was refluxed for 18 h, cooled to rt, diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried with Na2SO4, and concentrated in vacuo. Purification by medium pressure liquid chromatography (SiO2, 3:1 hexanes/ethyl acetate) gave 793 mg (65%) of the title compound. MS 223 (M+H)+.

Workup

  1. customprepared
  2. temperatureThe reaction mixture was refluxed for 18 h
  3. washwashed with sat. aq. NaHCO3 and brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by medium pressure liquid chromatography (SiO2, 3:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-9d3177504f114a249187e7f26560dc7c
Source dataset
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06825170B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes