Acetonitrile → HCID 58608143, compound

HRID 2243585Notes

Reaction equation

HRID 2243585 reaction equation
[CH2:1]([N:8]1[CH:13]=[CH:12][C:11](=[O:14])[C:10]2[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:16](I)[O:17][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)([OH:27])=[O:26].C(=O)([O-])[O-].[Na+].[Na+].CC#N>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.CCOC(C)=O>[CH2:1]([N:8]1[CH:13]=[CH:12][C:11](=[O:14])[C:10]2[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:16]([C:32]3[CH:33]=[C:28]([CH:29]=[CH:30][CH:31]=3)[C:25]([OH:27])=[O:26])[O:17][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 27339573-Carboxyphenylboronic acidHCID 58608105HCID 58608105, compound

Product 1

HCID 58608143HCID 58608143, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
85 °C

Procedure

To a mixture of iodide 4f (2.94 g, 6.89 mmol, 1.0 equiv), 3-carboxyphenylboronic acid (1.26 g, 7.57 mmol, 1.1 equiv), tetrakis(triphenylphosphine)palladium (0.796 g, 0.689 mmol, 0.1 equiv), and sodium carbonate (2.92 g, 27.6 mmol, 4.0 equiv), was added MeCN (30 mL) and H2O (30 mL). The slurry was heated at 85° C. for 8 h. After cooling to rt, EtOAc (ca. 100 mL) and H2O (ca. 50 mL) were added. The aqueous layer was separated, filtered, and acidified with 1N HCl. The resulting white precipitate was filtered to provide acid 4k. MS (MH+) 422; Calculated 421.1 for C27H19NO4.

Workup

  1. temperatureAfter cooling to rt
  2. customThe aqueous layer was separated
  3. filtrationfiltered
  4. filtrationThe resulting white precipitate was filtered

Sources & evidence

ORD record
ord-73ab7d618713449997160b95e27afd23
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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