Sodium Carbonate → HCID 18458919, compound

HRID 1780358Notes

Reaction equation

HRID 1780358 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].[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[C:2]1[CH:3]=[C:4]([O:9][CH2:10][CH: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]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 22872666HCID 22872666, compound

Product 1

HCID 18458919HCID 18458919, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-bromo-6-chloro-3-(1-BOC-2(R)-pyrrolidinylmethoxy)pyridine from Example 69a (310 mg, 0.87 mmol), 2-thienylboronic acid (167 mg, 1.3 mmol), 2M Na2CO3 (3 mL) and Pd(0) (32 mg) were mixed together in toluene (6 mL), and the mixture was heated at reflux for 4 hours. The mixture was cooled and extracted with chloroform. The CHCl3 was removed under reduced pressure, and the residue was chromatographed on a silica gel column, eluting with hexane/ethyl acetate 1:1 to afford the title compound (64 mg, 20% yield). MS (DCI/NH3) m/z 287 (M+H)+. 1 H NMR (CDCl3, 300 MHz) δ: 1.47 (s, 9H), 1.84-2.11 (m, 3H), 3.31-3.48 (m, 2H), 3.82-4.30 (m, 3H), 7.12 (dd, J=4.5, 6, 1H), 7.34-7.42 (m, 3H), 7.46-7.57 (m, 1H), 8.23 (d, J=3, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with chloroform
  5. customThe CHCl3 was removed under reduced pressure
  6. customthe residue was chromatographed on a silica gel column
  7. washeluting with hexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-694d8fe88c90425b9026cc08eb1bfefe
Source dataset
uspto-grants-1997_05
Patent number
US05629325

Reaction notes

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