Sodium Carbonate → HCID 68208398, compound

HRID 1918831Notes

Reaction equation

HRID 1918831 reaction equation
O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:13][C:14]1[C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18][CH:17]=[CH:16][C:15]=1[N:29]1[CH2:41][CH2:40][C:39]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:32]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[C:31]=2[C:30]1=[O:50].Cl[C:52]1[CH:53]=[C:54]([NH:67][C:68]2[CH:77]=[C:71]3[CH2:72][N:73]([CH3:76])[CH2:74][CH2:75][N:70]3[N:69]=2)[C:55](=[O:66])[N:56]([CH2:58][O:59][CH2:60][CH2:61][Si:62]([CH3:65])([CH3:64])[CH3:63])[N:57]=1>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.O>[CH3:13][C:14]1[C:19]([C:52]2[CH:53]=[C:54]([NH:67][C:68]3[CH:77]=[C:71]4[CH2:72][N:73]([CH3:76])[CH2:74][CH2:75][N:70]4[N:69]=3)[C:55](=[O:66])[N:56]([CH2:58][O:59][CH2:60][CH2:61][Si:62]([CH3:63])([CH3:65])[CH3:64])[N:57]=2)=[CH:18][CH:17]=[CH:16][C:15]=1[N:29]1[CH2:41][CH2:40][C:39]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:32]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[C:31]=2[C:30]1=[O:50]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 58043885HCID 58043885, compoundHCID 67016170HCID 67016170, compound

Product 1

HCID 68208398HCID 68208398, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer, reflux condenser and nitrogen inlet was charged with 1,4-dioxane (5 mL), water (1 mL) and sodium carbonate (143 mg, 1.35 mmol). After bubbling nitrogen through the resulting mixture for 30 min, 117c (240 mg, 0.451 mmol), 117e (185 mg, 0.451 mmol) and tetrakis(triphenylphosphine)palladium(0) (52 mg, 0.045 mmol) were added, and the reaction mixture was heated at 100° C. for 3 h. After this time, the reaction was cooled to room temperature and partitioned between water (25 mL) and methylene chloride (50 mL). The organic layer was separated, washed with brine (75 mL) and dried over sodium sulfate. The drying agent was removed by filtration, and the filtrate was concentrated under reduced pressure to a dark oil, which was purified by flash chromatography to afford an 89% yield (315 mg) of 117f as a yellow oil: 1H NMR (500 MHz, CDCl3) d 7.88 (s, 1H), 7.66 (d, 1H, J=8.0 Hz), 7.45 (m, 3H), 7.39 (t, 1H, J=8.0 Hz), 7.34 (d, 1H, J=8.0 Hz), 7.24 (t, 2H, J=8.0 Hz), 6.12 (d, 1H, J=10.5 Hz), 6.05 (d, 1H, J=10.5 Hz), 5.69 (s, 1H), 5.63 (d, 1H, J=10.5 Hz), 5.52 (d, 1H, J=10.5 Hz), 4.09 (m, 2H), 3.88 (m, 2H), 3.75 (m, 2H), 3.68 (s, 3H), 3.59 (m, 2H), 3.26-3.17 (m, 4H), 2.61 (m, 2H), 2.29 (s, 3H), 0.98 (t, 2H, J=8.0 Hz), 0.85 (t, 2H, J=8.0 Hz), −0.01 (s, 9H), −0.07 (s, 9H); MS (ESI+) m/z 781.4 (M+H).

Workup

  1. customA 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. temperaturereflux condenser and nitrogen inlet
  3. customAfter bubbling nitrogen through the resulting mixture for 30 min
  4. temperatureAfter this time, the reaction was cooled to room temperature
  5. custompartitioned between water (25 mL) and methylene chloride (50 mL)
  6. customThe organic layer was separated
  7. washwashed with brine (75 mL)
  8. dry with materialdried over sodium sulfate
  9. customThe drying agent was removed by filtration
  10. concentrationthe filtrate was concentrated under reduced pressure to a dark oil, which
  11. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-47237fd83a144274ae0777d1a1c19c10
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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