Tetrahydrofuran → HCID 11335358, compound

HRID 1454778Notes

Reaction equation

HRID 1454778 reaction equation
Br[C:2]1[N:7]=[C:6]([CH2:8][N:9]2[CH:15]3[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]3)[CH2:11][CH2:10]2)[CH:5]=[CH:4][CH:3]=1.C1COCC1.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>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.C(O)C>[C:23]1([C:2]2[N:7]=[C:6]([CH2:8][N:9]3[CH:15]4[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]4)[CH2:11][CH2:10]3)[CH:5]=[CH:4][CH:3]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 714066324-[(6-Bromopyridin-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane

Product 1

HCID 11335358HCID 11335358, compoundYield 27.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 4-(6-bromo-pyridin-2-ylmethyl)-1,4-diaza-bicyclo[3.2.2]nonane (17.0 mg, 0.06 mmol) in a solvent mixture of THF, ethanol, and water (6.0 mL of 1:1:1) was added phenylboronic acid (18 mg, 0.15 mmol), potassium carbonate (70 mg), and a catalytic amount of tetrakis(triphenylphosphine)palladium(0). The mixture was heated at reflux temperature for 3 hours, cooled, and concentrated to near dryness. The residue was triturated with chloroform (3×) and the crude product in chloroform subjected silica gel chromatography eluting with a chloroform (ammoniated) to 5% methanollchloroform gradient to give the title compound as an off-white solid (4.8 mg). MS (ES+) 294 (MH+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 3 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. customThe residue was triturated with chloroform (3×)
  6. washeluting with a chloroform (ammoniated) to 5% methanollchloroform gradient

Sources & evidence

ORD record
ord-735ff0d6326048bcadc39dafebb4128f
Source dataset
uspto-grants-2009_01
Patent number
US07482338B2

Reaction notes

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