Sodium Carbonate → HCID 58415370, compound

HRID 2075166Notes

Reaction equation

HRID 2075166 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][C:3]=1B(O)O.[CH2:13]([C:20]1[O:21][C:22]2[CH:28]=[CH:27][C:26](Br)=[CH:25][C:23]=2[CH:24]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:13]([C:20]1[O:21][C:22]2[CH:28]=[CH:27][C:26]([C:3]3[CH:4]=[CH:5][C:6]([CH:8]=[O:9])=[CH:7][C:2]=3[F:1])=[CH:25][C:23]=2[CH:24]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 162180452-Fluoro-4-formylbenzeneboronic acidHCID 227689092-Benzyl-5-bromo-1-benzofuran

Product 1

HCID 58415370HCID 58415370, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-fluoro-4-formylphenylboronic acid (58 mg, 0.348 mmol), 2-benzyl-5-bromobenzofuran (50 mg, 0.174 mmol), tetrakis(triphenylphosphine) palladium(0) (20 mg, 0.0174 mmol) and sodium carbonate (106 mg, 1.0 mmol) in 1,4-dioxane (4 mL) and water (1 mL) was heated at 100° C. for 12 h. The mixture was partitioned between brine (20 mL) and EtOAc (20 mL). The organic layer was dried. Removal of solvents gave the residue which was purified by silica gel column chromatography (ISCO system, 30% dichloromethane in hexanes) to give the product as a off white solid: 1H NMR (400 MHz, CDCl3) δ 10.0 (s, 1H), 7.61-7.75 (m, 5H), 7.27-7.51 (m, 7H), 6.45 (s, 1H), 4.14 (s, 2H).

Workup

  1. customThe mixture was partitioned between brine (20 mL) and EtOAc (20 mL)
  2. customThe organic layer was dried
  3. customRemoval of solvents
  4. customgave the residue which
  5. customwas purified by silica gel column chromatography (ISCO system, 30% dichloromethane in hexanes)
  6. customto give the product as a off white solid

Sources & evidence

ORD record
ord-2b0043bee3f44d369723d74443f33815
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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