Sodium Carbonate → HCID 16041929, compound

HRID 545172Notes

Reaction equation

HRID 545172 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:30](=[CH:31][CH:32]=1)[O:29][C:7]1([CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]4[C:17](=[C:18]([O:27][CH3:28])[CH:19]=[CH:20][CH:21]=4)[N:16]=3)=[O:14])[CH2:9][CH2:8]1)[CH2:6][C:5]2=[O:33].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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>[CH3:26][O:25][C:23]1[C:22]2[C:17](=[C:18]([O:27][CH3:28])[CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:13]([N:10]2[CH2:9][CH2:8][C:7]3([CH2:6][C:5](=[O:33])[C:4]4[C:30](=[CH:31][CH:32]=[C:2]([C:8]5[CH:9]=[N:10][CH:11]=[CH:12][CH:7]=5)[CH:3]=4)[O:29]3)[CH2:12][CH2:11]2)=[O:14])[CH:24]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 16041747HCID 16041747, compound

Product 1

HCID 16041929HCID 16041929, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

6-Bromo-1′-[(4,8-dimethoxyquinolin-2-yl)carbonyl]spiro[chroman-2,4′-piperidin]-4-one (200 mg), pyridine-3-boronic acid-1′,3′-propanediol cyclic ester (76.6 mg) and Pd(PPh3)4 (45.2 mg) were suspended in a mixture of 1,4-dioxane (1.6 mL) and aqueous 2 M sodium carbonate solution (0.8 mL), and heated under reflux at 110° C. for 12 hours. The reaction solution was partitioned between ethyl acetate and water, extracted with ethyl acetate, washed with saturated brine, and dried with magnesium sulfate. The desiccant was removed through filtration, the filtrate was concentrated under reduced pressure, and the resulting residue was purified through thin-layer chromatography (chloroform/methanol=95/5) to obtain the intended compound. 1H-NMR (300 MHz, CDCl3) δ: 8.83 (1H, d, J=1.7 Hz), 8.59 (1H, dd, J=4.8, 1.7 Hz), 8.10 (1H, d, J=2.4 Hz), 7.82-7.90 (1H, m), 7.77 (1H, m), 7.76 (1H, d, J=8.6, 2.4 Hz), 7.47 (1H, dd, J=8.2, 7.8 Hz), 7.36 (1H, dd, J=7.8, 4.8 Hz), 7.19 (1H, s), 7.15 (1H, d, J=8.6 Hz), 7.08 (1H, d, J=7.8 Hz), 4.55-4.65 (1H, m), 4.10-4.25 (1H, m), 4.08 (3H, s), 4.03 (3H, s), 3.55-3.70 (1H, m), 3.30-3.45 (1H, m), 2.87 (1H, d, J=16.7 Hz), 2.80 (1H, d, J=16.7 Hz), 2.20-2.30 (1H, m), 2.05-2.20 (1H, m), 1.80-2.00 (2H, m). MS [M]+=509.

Workup

  1. temperatureheated
  2. customThe reaction solution was partitioned between ethyl acetate and water
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customThe desiccant was removed through filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe resulting residue was purified through thin-layer chromatography (chloroform/methanol=95/5)
  9. customto obtain the intended compound

Sources & evidence

ORD record
ord-3c5f53c63ff34eb48d5b65b02803afb0
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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