Sodium Carbonate → HCID 66743454, compound

HRID 505109Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[Br:8][C:9]1[CH:17]=[C:16](B(O)O)[C:12]2[O:13][CH2:14][CH2:15][C:11]=2[CH:10]=1.C([O-])([O-])=O.[Na+].[Na+].[NH4+].[Cl-]>COCCOC.CCO.COCCOC.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>[Br:8][C:9]1[CH:17]=[C:16]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[C:12]2[O:13][CH2:14][CH2:15][C:11]=2[CH:10]=1

Participants

Conditions

Temperature: 50 °C

Procedure

4-Bromopyridine or hydrochloride salt thereof was dissolved in DME under argon and Pd(Ph3P)4 (3 mol %) was added. The mixture was stirred for 10 min at 50° C. To this solution was added (commercially available) 5-bromo-2,3-dihydrobenzo[b]furan-7-boronic acid dissolved in a minimum amount of EtOH/DME 1:2 followed by 2N Na2CO3. The reaction mixture was refluxed (110° C.) under stirring for 2 h. The flask was cooled to RT, the mixture was treated with sat. aq. NH4Cl solution and extracted with CHCl3. Evaporation and purification by SiO2 gel chromatography (hexane/ethyl acetate: 4/1) gave the title compound in 76% yield.

Workup

temperatureThe reaction mixture was refluxed (110° C.)
stirringunder stirring for 2 h
temperatureThe flask was cooled to RT
extractionextracted with CHCl3
customEvaporation and purification by SiO2 gel chromatography (hexane/ethyl acetate: 4/1)

Sources & evidence

ORD record: ord-bf719ac7a442458b8c40406b78230662
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781436B2

Reaction notes

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