Sodium Carbonate → HCID 22002655, compound

HRID 325193Notes

Reaction equation

HRID 325193 reaction equation
[O:1]=[C:2]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:8](OS(C(F)(F)F)(=O)=O)[C:4]2([CH2:7][CH2:6][CH2:5]2)[O:3]1.[CH3:24][S:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C([O-])([O-])=O.[Na+].[Na+].[NH4+].[Cl-]>C1COCC1.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>[CH3:24][S:25][C:26]1[CH:31]=[CH:30][C:29]([C:8]2[C:4]3([CH2:5][CH2:6][CH2:7]3)[O:3][C:2](=[O:1])[C:9]=2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 27339594-(Methylthio)phenylboronic acidHCID 86756644HCID 86756644, compound

Product 1

HCID 22002655HCID 22002655, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of the triflate (550 mg, 1.58 mmol) from step 2 in THF (10 ml) and boronic acid from step 3 (318 mg, 1.90 mmol) was added an aq. solution of Na2CO3 (2.0M, 3.16 mmol, 1.60 ml) and Pd(PPh3)4 (91 mg, 0.079 mmol). The mixture was heated for 2 h at 70° C., cooled and poured into sat. aq. NH4Cl. The aq. layer was extracted with Et2O and the combined org. layers were dried over MgSO4. Purification via flash chromatography (20% EtOAc in hexane) gave 460 mg of the title compound as a foam.

Workup

  1. temperaturecooled
  2. extractionThe aq. layer was extracted with Et2O
  3. dry with materiallayers were dried over MgSO4
  4. customPurification via flash chromatography (20% EtOAc in hexane)

Sources & evidence

ORD record
ord-5cd8a607201e446fb02b075d4fe5be69
Source dataset
uspto-grants-2001_04
Patent number
US06222048B1

Reaction notes

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