Sodium Carbonate → HCID 22872651, compound

HRID 1780360Notes

Reaction equation

HRID 1780360 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Br[C:12]1[CH:13]=[C:14]([O:18][CH2:19][C@H:20]2[CH2:24][CH2:23][CH2:22][N:21]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:15]=[N:16][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[NH2:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:13]=[C:14]([O:18][CH2:19][C@H:20]3[CH2:24][CH2:23][CH2:22][N:21]3[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:15]=[N:16][CH:17]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 922693-Aminophenylboronic acidHCID 154802363-bromo-5-[[1-(tert-butoxycarbonyl)-2(R)-pyrrolidinyl]methoxy]pyridine

Product 1

HCID 22872651HCID 22872651, compoundYield 148.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-aminophenylboronic acid (366 mg, 2.36 mmol, Aldrich Chem. Co.) and 5-bromo-3-(1-BOC-2-(R)-pyrrolidinylmethoxy)-pyridine (560 mg, 1.57 mmol) in toluene (10 mL) was added Pd(0) (58 mg) and Na2CO3 (5 mL of a 2M solution), and the mixture was heated at reflux. The solvent was removed under vacuum, and the residue was extracted with ethyl acetate and chloroform. The organic extracts were dried over MgSO4 and concentrated. The residue was chromatographed on a silica gel column, eluting with ethyl acetate hexane 1:1 to afford to give the title compound (860 mg, 100% yield). MS (DCI/NH3) m/z 370 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 1.48 (s, 9h), 1.84-2.13 (m, 4H), 3.28-3.51 (m, 2H), 3.70-4.08 (m, 2H), 4.08-4.29 (m, 2H), 6.70-6.75 (m, 1H), 6.85-7.03 (m, 2H), 7.31-7.50 (m, 2H), 7.50-7.72 (m, 1H), 8.29 (d, J=3.0, 1H), 8.443 (br s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customThe solvent was removed under vacuum
  4. extractionthe residue was extracted with ethyl acetate and chloroform
  5. dry with materialThe organic extracts were dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was chromatographed on a silica gel column
  8. washeluting with ethyl acetate hexane 1:1
  9. customto afford

Sources & evidence

ORD record
ord-e62fd4871b594d91bc1408427ba7a0ff
Source dataset
uspto-grants-1997_05
Patent number
US05629325

Reaction notes

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