Sodium Carbonate → HCID 22872654, compound

HRID 365848Notes

Reaction equation

HRID 365848 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]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[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>[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][N:12]3[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[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 22872654HCID 22872654, compoundYield 29.8%

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 (CDC13, 300 MHz) δ1.44 (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-eae4f0db95f84fa490224f6b650d5d20
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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