Sodium Carbonate → HCID 12050296, compound

HRID 993421Notes

Reaction equation

HRID 993421 reaction equation
Br[C:2]1[CH:20]=[C:19]([Cl:21])[C:5]([O:6][C@H:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]([O:10][CH3:11])=[O:9])=[C:4]([Cl:22])[CH:3]=1.[CH:23]1[C:31]2[C:30]3[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=3[O:28][C:27]=2[C:26](B(O)O)=[CH:25][CH:24]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=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>[Cl:21][C:19]1[CH:20]=[C:2]([C:35]2[C:29]3[O:28][C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:31]=4[C:30]=3[CH:32]=[CH:33][CH:34]=2)[CH:3]=[C:4]([Cl:22])[C:5]=1[O:6][C@H:7]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734328Dibenzofuran-4-boronic acidHCID 12050295HCID 12050295, compound

Product 1

HCID 12050296HCID 12050296, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of Example 1A (944 mg, 2.34 mmol), dibenzo(b,d)furan-4-ylboronic acid (619 mg, 2.92 mmol), Pd(PPh3)4 (216 mg, 0.187 mmol), and 2M Na2CO3 (5 mL, 10 mmol) in toluene (10 mL) was heated to 78° C., stirred for 18 hours, cooled to room temperature, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/hexanes to provide 1.05 g (91%) of the desired product.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-0e0909064f704e15945e34278693c4cc
Source dataset
uspto-grants-2002_10
Patent number
US06472545B2

Reaction notes

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