Sodium Carbonate → HCID 66750251, compound

HRID 75409Notes

Reaction equation

HRID 75409 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:14][CH:13]3[O:15][CH:10]([CH2:11][CH2:12]3)[CH2:9]2)[CH:5]=[CH:4][N:3]=1.[NH2:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO>[CH:10]12[O:15][CH:13]([CH2:12][CH2:11]1)[CH2:14][N:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:20]3[CH:21]=[CH:22][C:17]([NH2:16])=[CH:18][CH:19]=3)[N:7]=1)[CH2:9]2

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27346154-Aminophenylboronic acidHCID 663715273-(2-Chloropyrimidin-4-yl)-8-oxa-3-azabicyclo[3,2,1]octane

Product 1

HCID 66750251HCID 66750251, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

3-(2-Chloro-pyrimidin-4-yl)-8-oxa-3-aza-bicyclo[3.2.1]octane (3, 564 mg, 2.5 mmol) and 4-aminophenylboronic acid, pinacol ester (602 mg, 2.75 mmol) are dissolved in toluene (25 mL) and EtOH (15 mL). A 2M solution of Na2CO3 is added (5 mL) and the mixture is degassed by leading a stream of nitrogen through the solution. Tetrakis(triphenylphosphine) palladium is added (144 mg, 5 mol %) and the mixture is heated under reflux for 48 hours. The mixture is diluted with EtOAc, washed with saturated NaHCO3, the organic phase is dried (MgSO4), filtered, and concentrated. The mixture is purified by silica gel chromatography using a gradient of ethyl acetate in hexanes (40-100%) to give 576 mg (2.04 mmol, 82%) of 4-[4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)pyrimidin-2-yl]aniline. RT 1.51, M+H=283.1

Workup

  1. customthe mixture is degassed
  2. additionTetrakis(triphenylphosphine) palladium is added (144 mg, 5 mol %)
  3. temperaturethe mixture is heated
  4. temperatureunder reflux for 48 hours
  5. additionThe mixture is diluted with EtOAc
  6. washwashed with saturated NaHCO3
  7. dry with materialthe organic phase is dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe mixture is purified by silica gel chromatography

Sources & evidence

ORD record
ord-5909c2317c71454cb3ca4a0b4656bfdd
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Reaction notes

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