Sodium Carbonate → HCID 71263274, compound

HRID 332665Notes

Reaction equation

HRID 332665 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:40])[NH:11][CH:12]([C:19]1[CH:24]=[C:23](Br)[CH:22]=[C:21]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]3[O:39][CH2:38][CH2:37][O:36]3)[CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:2]2.[C:41]1(B(O)O)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:40])[NH:11][CH:12]([C:19]1[CH:24]=[C:23]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:22]=[C:21]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]3[O:39][CH2:38][CH2:37][O:36]3)[CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:2]2

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 71263288HCID 71263288, compound

Product 1

HCID 71263274HCID 71263274, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of (R)-quinuclidin-3-yl((3-((8-(1,3-dioxolan-2-yl)octyl)oxy)-5-bromophenyl)(phenyl)methyl)carbamate (0.2 g, 0.33 mmol) (prepared in Example 28 Step 8) in toluene (4 mL) and water (1 mL), was added phenyl boronic acid (0.04 g, 0.33 mmol), sodium carbonate (0.07 g, 0.66 mmol), and tetrakis(triphenylphosphine)palladium (0) (0.04 g, 0.03 mmol). The reaction mixture was heated in the microwave at 120° C. for 30 minutes. The solvent was removed under reduced pressure, diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were dried (sodium sulphate), filtered and solvent removed under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-10% methanol in ethyl acetate to afford the title compound as a colourless oil (0.14 g, 71%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate (×3)
  4. dry with materialThe combined organic extracts were dried (sodium sulphate)
  5. filtrationfiltered
  6. customsolvent removed under reduced pressure
  7. customThe crude material was purified by silica gel chromatography
  8. washeluting with 0-10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-546332c8514b487092c6d855945a0c7e
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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