Phenylboronic Acid → HCID 86585105, compound

HRID 914930Notes

Reaction equation

HRID 914930 reaction equation
I[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[O:27]1[CH2:32]COCC1.C(COC)[O:34]C>C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[CH:32]([OH:27])=[O:34].[CH3:12][C:8]1[CH:7]=[C:6]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:5]2[C:10](=[CH:11][C:2]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:3][CH:4]=2)[N:9]=1

Participants

5

Reactant 3

HCID 66827Phenylboronic AcidHCID 113366637-Iodo-2-methyl-4-pyrrolidin-1-yl-quinolineHCID 68454173Dioxane dimethoxyethane

Product 1

HCID 86585105HCID 86585105, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 53485975CID 53485975Catalyst

Conditions

Temperature
85 °C

Procedure

To a solution of 43 mg (0.13 mmol) 7-Iodo-2-methyl-4-pyrrolidin-1-yl-quinoline in 1.2 ml dioxane/dimethoxyethane 1:1 was added 39.6 mg (0.325 mmol) phenyl-boronic acid, 6 mg (0.007 mmol) Dichloro[1,1′-Bis(diphenylphosphino)-ferrocene]palladium (II) dichloromethan adduct, and 0.55 ml 2M Na2CO3aq. and the mixture was heated to 85° C. for 12 h. After filtration the mixture was purified by reversed phase column chromatography eluting with an acetonitrile/water (formic acid) gradient yielding 25 mg (57%) of the title compound. MS m/e (%): 289.4 (MH+, 100).

Workup

  1. filtrationAfter filtration the mixture
  2. customwas purified by reversed phase column chromatography
  3. washeluting with an acetonitrile/water (formic acid) gradient

Sources & evidence

ORD record
ord-3fce8974e99c4e08bb133726f8b1a60c
Source dataset
uspto-grants-2007_09
Patent number
US07265125B2

Reaction notes

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