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Diethylamine → L-776967

HRID 1940130
Notes
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Reaction equation

HRID 1940130 reaction equation
Br[C:2]1[C:3](=[O:17])[CH2:4][CH2:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=1.[F:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[C:23]([F:25])[CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(NCC)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[F:18][C:19]1[CH:20]=[C:21]([C:2]2[C:3](=[O:17])[CH2:4][CH2:5][C:6]=2[C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[CH:22]=[C:23]([F:25])[CH:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 10663122HCID 10663122, compound

Product 1

HCID 9798392L-776967Yield 30.3%

Reagents, catalysts & solvents 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 1140TolueneSolvent

Procedure

To a mixture of 2-bromo-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one (664 mg, 2.11 mmol), 3,5-difluorophenylboronic acid (832 mg, 5.27 mmol), tris(dibenzylideneacetone)dipalladium(0) (83 mg, 0.09 mmol), and triphenylphosphine (96 mg, 0.36 mmol) was added 40 mL of 3:1:1 toluene:n-propanol:water and the mixture was purged with nitrogen. After stirring 10 min, diethylamine (1.1 mL, 10.6 mmol) was added and the solution was heated to reflux for 4 h. The mixture was cooled and partitioned between 1M NaOH and EtOAc. The organic phase was washed with water, 1M HCl and brine, and dried over MgSO4. Purification by silica gel chromatography, eluting with 50% CH2Cl2 /hexanes, followed by crystallization from CH2Cl2 /ether/hexanes gave the title compound (223 mg).

Workup

  1. customn-propanol:water and the mixture was purged with nitrogen
  2. temperaturethe solution was heated
  3. temperatureto reflux for 4 h
  4. temperatureThe mixture was cooled
  5. custompartitioned between 1M NaOH and EtOAc
  6. washThe organic phase was washed with water, 1M HCl and brine
  7. dry with materialdried over MgSO4
  8. customPurification by silica gel chromatography
  9. washeluting with 50% CH2Cl2 /hexanes
  10. customfollowed by crystallization from CH2Cl2 /ether/hexanes

Sources & evidence

ORD record
ord-3c818dd8062f4129a9454d55bf04e16e
Source dataset
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05698584

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes