Sodium Carbonate → HCID 67995873, compound

HRID 1907806Notes

Reaction equation

HRID 1907806 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:11]=[N:12][C:13]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[CH:14][CH:15]=2)[C:5](=[O:8])[NH:6][N:7]=1.[C:22]([C:26]1[N:27]=[CH:28][C:29]([C:32]([NH:34][C:35]2[CH:40]=[C:39](B3OC(C)(C)C(C)(C)O3)[CH:38]=[CH:37][C:36]=2[F:50])=[O:33])=[N:30][CH:31]=1)([CH3:25])([CH3:24])[CH3:23].C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C(OCC)(=O)C.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.CN(C=O)C>[C:22]([C:26]1[N:27]=[CH:28][C:29]([C:32]([NH:34][C:35]2[CH:40]=[C:39]([C:2]3[CH:3]=[C:4]([NH:9][C:10]4[N:11]=[N:12][C:13]([C:16]5[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=5)=[CH:14][CH:15]=4)[C:5](=[O:8])[NH:6][N:7]=3)[CH:38]=[CH:37][C:36]=2[F:50])=[O:33])=[N:30][CH:31]=1)([CH3:25])([CH3:23])[CH3:24]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 58540168HCID 58540168, compoundHCID 58540266HCID 58540266, compound

Product 1

HCID 67995873HCID 67995873, compoundYield 49%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A 15-mL pressure tube equipped with a magnetic stirrer and screw cap with a septum was charged with 6e (90 rug, 0.30 mmol), 6f (156 mg, 0.39 mmol), sodium carbonate (95 mg, 0.90 mmol), water (0.5 mL), 1,4-dioxane (1.8 mL), and DMF (0.9 mL). After bubbling nitrogen through the resulting suspension for 30 min, tetrakis(triphenylphosphine)palladium(0) (35 mg, 0.03 mmol) was added; the tube was sealed, and the reaction mixture was heated for 16 h in a 120° C. bath. After this time, the mixture was cooled to room temperature and diluted with ethyl acetate (50 mL) and water (5 mL). The organic layer was separated and concentrated under reduced pressure. The residue was purified by column chromatography on silica to afford a 49% yield (79 mg) of 6g as an off-white solid: mp>300° C.; 1H NMR (500 MHz, DMSO-d6) δ 13.40 (s, 1H), 10.45 (s, 1H), 9.93 (s, 1H), 9.25 (s, 1H), 9.04 (s, 1H), 8.95 (s, 1H), 8.74 (d, 2H, J=3.3 Hz), 8.54 (d, 1H, J=4.2 Hz), 8.33 (d, 1H, J=5.7 Hz), 8.10 (d, 2H, J=3.0 Hz), 8.02 (d, 1H, J=5.4 Hz), 7.69 (m, 1H), 7.53 (m, 1H), 1.43 (s, 9H); MS (ESI+) m/z 538.2 (M+H).

Workup

  1. customA 15-mL pressure tube equipped with a magnetic stirrer
  2. customscrew cap with a septum
  3. customAfter bubbling nitrogen through the resulting suspension for 30 min
  4. customthe tube was sealed
  5. temperatureAfter this time, the mixture was cooled to room temperature
  6. customThe organic layer was separated
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-a404f1bf32084c5eb239d8ce707a39fe
Source dataset
uspto-grants-2013_12
Patent number
US08598174B2

Reaction notes

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