1,2-Dimethoxyethane → 1-[5-fluoro-3-(3-fluoro-benzyl)-7-(1-triisopropylsilanyl-1H-pyrrol-3-yl)-benzofuran-2-yl]-ethanone

HRID 18194

Reaction equation

HRID 18194 reaction equation
Br[C:2]1[C:10]2[O:9][CH:8]=[C:7]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=3)[C:6]=2[CH:5]=[C:4]([F:19])[CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:28]([Si:31]([CH:43]([CH3:45])[CH3:44])([CH:40]([CH3:42])[CH3:41])[N:32]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33]1)([CH3:30])[CH3:29].C[O:47][CH2:48][CH2:49]OC>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[F:19][C:4]1[CH:3]=[C:2]([C:34]2[CH:35]=[CH:36][N:32]([Si:31]([CH:43]([CH3:45])[CH3:44])([CH:40]([CH3:42])[CH3:41])[CH:28]([CH3:30])[CH3:29])[CH:33]=2)[C:10]2[O:9][C:8]([C:48](=[O:47])[CH3:49])=[C:7]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=3)[C:6]=2[CH:5]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 62657Potassium Phosphate, TribasicHCID 27633031-(Triisopropylsilyl)pyrrole-3-boronic acidHCID 593449097-Bromo-5-fluoro-3-(3-fluoro-benzyl)-benzofuran

Product 1

HCID 593449101-[5-fluoro-3-(3-fluoro-benzyl)-7-(1-triisopropylsilanyl-1H-pyrrol-3-yl)-benzofuran-2-yl]-ethanoneYield 75%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a flask was added 7-bromo-5-fluoro-3-(3-fluoro-benzyl)-benzofuran (0.365 gm, 1.0 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (0.010 gm, 0.012 mmol), potassium phosphate (0.425 gm, 2.0 mmol), 1-(triisopropylsilyl)pyrrole-3-boronic acid (0.365 gm, 1.37 mmol), DME (12 ml) and water (2 ml). The mixture was evacuated and refilled with nitrogen while being sonicated. The mixture was heated in a microwave reactor for 15 minutes at 70° C., then for 15 minutes at 100° C., and then for 15 minutes at 130° C. The mixture was cooled, concentrated under reduced pressure, diluted with brine and extracted with ethyl acetate. The organic phase was absorbed onto a pad of silica gel that was rinsed with ethyl acetate/hexanes (250 ml, 1/9) and eluted to give 1-[5-fluoro-3-(3-fluoro-benzyl)-7-(1-triisopropylsilanyl-1H-pyrrol-3-yl)-benzofuran-2-yl]-ethanone (0.38 gm, 75% yield).

Workup

  1. customThe mixture was evacuated
  2. additionrefilled with nitrogen
  3. customwhile being sonicated
  4. waitfor 15 minutes at 130° C
  5. temperatureThe mixture was cooled
  6. concentrationconcentrated under reduced pressure
  7. additiondiluted with brine
  8. extractionextracted with ethyl acetate
  9. customThe organic phase was absorbed onto a pad of silica gel that
  10. washwas rinsed with ethyl acetate/hexanes (250 ml, 1/9)
  11. washeluted

Sources & evidence

ORD record
ord-769ada0d2a334d929efe39d644428bb9
Source dataset
uspto-grants-2010_06
Patent number
US07741326B2

Linked notes

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