Sodium Carbonate → HCID 86758469, compound

HRID 2305130Notes

Reaction equation

HRID 2305130 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:9][CH2:10][C@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2C(OC(C)(C)C)=O)[CH:5]=[N:6][C:7]=1[Cl:8].[NH2:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[ClH:8].[ClH:8].[NH2:23][C:24]1[CH:29]=[C:28]([C:2]2[CH:3]=[C:4]([O:9][CH2:10][C@H:11]3[CH2:15][CH2:14][CH2:13][NH:12]3)[CH:5]=[N:6][C:7]=2[Cl:8])[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 922693-Aminophenylboronic acidHCID 22872666HCID 22872666, compound

Product 1

HCID 86758469HCID 86758469, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5-bromo-6-chloro-3-(1-BOC-2-(R)-pyrrolidinylmethoxy)pyridine from Example 69a (520 mg, 1.33 mmol) and 3-aminophenylboronic acid (310 mg, 2.0 mmol) in toluene (8 mL) was added Pd(0) (50 mg) and Na2CO3 (2.5 mL of a 2 M solution), and the mixture was heated at reflux for 16 hours. The solvent was removed under vacuum, and the residue was purified by chromatography on a silica gel column, eluting with CHCl3:Et2O 100:5-100:40 to afford 160 mg of the title compound. MS (CI/NH3) m/z 404 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 1.44 (s, 9H), 1.88 (m, 1H), 2.03 (m, 2H), 3.37 (m, 2H), 3.76 (m, 2H), 4.16 (m, 2H), 6.75 (m, 2H), 6.82 (m, 1H), 7.22 (m, 2H), 8.08 (m, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified by chromatography on a silica gel column
  5. washeluting with CHCl3:Et2O 100:5-100:40

Sources & evidence

ORD record
ord-ad909e28bdf54432891626c563e93561
Source dataset
uspto-grants-2002_08
Patent number
US06437138B1

Reaction notes

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