p-Bromoacetophenone → HCID 66939490, compound

HRID 1257405Notes

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]

Participants

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

customThe palladium catalyst was removed by filtration
customthe solvent was evaporated under reduced pressure
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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