Sodium Carbonate → HCID 117680428, compound

HRID 332685Notes

Reaction equation

HRID 332685 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:35])[NH:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31](Br)=[CH:30][CH:29]=3)[CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:2]2.[CH:36]([C:38]1[CH:43]=[CH:42][C:41](B(O)O)=[CH:40][CH:39]=1)=[O:37].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:35])[NH:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([C:41]4[CH:42]=[CH:43][C:38]([CH:36]=[O:37])=[CH:39][CH:40]=4)=[CH:30][CH:29]=3)[CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:2]2

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 71113091HCID 71113091, compound

Product 1

HCID 117680428HCID 117680428, compoundYield 41.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

(R)-quinuclidin-3-yl((3-(4-bromophenethoxy)phenyl)(phenyl)methyl)carbamate (0.40 g, 0.747 mmol), 4-formylphenylboronic acid (0.123 g, 0.822 mmol), and sodium carbonate (0.158 g, 1.494 mmol) were combined in toluene (9.94 mL) and water (2.48 mL). The mixture was degassed with nitrogen for 10 minutes. Tetrakis-(triphenylphosphine)palladium(0) (0.087 g, 0.075 mmol) was added, and the mixture heated at 120° C. for 30 minutes in a microwave. The mixture was filtered, and the filtrate partitioned between ethyl acetate and water. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to afford a brown oil. The crude material was partially purified using a flash C18 cartridge eluting with 30-60% acetonitrile in water to afford a brown oil (0.174 g). The material was used directly in the next step with no further purification.

Workup

  1. customThe mixture was degassed with nitrogen for 10 minutes
  2. filtrationThe mixture was filtered
  3. customthe filtrate partitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford a brown oil
  8. customThe crude material was partially purified
  9. washeluting with 30-60% acetonitrile in water

Sources & evidence

ORD record
ord-d2aa924f281549e0997395cd86283e67
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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