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p-Bromoacetophenone → HCID 66939490, compound

HRID 1257405
Notes
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Reaction equation

HRID 1257405 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[N:14]=[C:15]([CH2:18][N:19]3[CH:23]=[C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:21]=[N:20]3)[S:16][CH:17]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)#[CH:2].[CH3:29][C:30]([C:32]1[CH:37]=[CH:36][C:35](Br)=[CH:34][CH:33]=1)=[O:31].C(N(CC)CC)C>CN(C)C=O.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>[C:30]([C:32]1[CH:37]=[CH:36][C:35]([C:2]#[C:1][C:3]2[CH:4]=[C:5]([C:13]3[N:14]=[C:15]([CH2:18][N:19]4[CH:23]=[C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:21]=[N:20]4)[S:16][CH:17]=3)[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=2)=[CH:34][CH:33]=1)(=[O:31])[CH3:29]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7466p-BromoacetophenoneHCID 8471TriethylamineHCID 86650596HCID 86650596, compound

Product 1

HCID 66939490HCID 66939490, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
90 °C

Procedure

In the same manner as in Example 98c, to a solution (3 mL) of the compound (200 mg, 0.49 mmol) obtained in Example 98b, 4-bromoacetophenone (150 mg, 0.74 mmol), triethylamine (0.14 mL, 0.98 mmol) and copper iodide(I) (19 mg, 0.10 mmol) in N,N-dimethylformamide was added tetrakistriphenylphosphinepalladium (58 mg, 0.050 mmol), and the mixture was stirred at 90° C. overnight. The palladium catalyst was removed by filtration and the solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=75/25) to give the title compound (97 mg, 38%) as a pale-yellow solid.

Workup

  1. customThe palladium catalyst was removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=75/25)

Sources & evidence

ORD record
ord-fa11e24661ba493a959e03bb40ea4f66
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08461348B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes