3-Bromodiphenyl ether → HCID 23130742, compound

HRID 2080261Notes

Reaction equation

HRID 2080261 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11](=[O:13])[CH3:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[O:14]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23](Br)[CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CC(C)([O-])C.[K+]>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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O1CCCC1>[O:14]([C:21]1[CH:26]=[C:25]([CH2:12][C:11]([C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:1]=[CH:2][CH:3]=[CH:4]3)=[O:13])[CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 961653-Bromodiphenyl etherHCID 2585591-(Quinolin-6-yl)ethan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 23130742HCID 23130742, compoundYield 19%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

According to an analogous method to Example W-3, 1-quinolin-6-yl-ethanone described in Preparation Example 131 (171 mg, 1 mmol), 1-phenoxy-3-bromobenzene (274 mg, 1.1 mmol), bis(dibenzylideneacetone)palladium (10 mg, 0.0187 mmol), 1,1′-bis(diphenylphosphino)ferrocene (12.5 mg, 0.0225 mmol), potassium tert-butoxide (236 mg, 2.1 mmol) and tetrahydrofuran (15 mL) were stirred at 70° C. for 6 hours under nitrogen atmosphere, and the title compound (64 mg, 0.189 mmol, 19%) was obtained as a pale yellow oily substance.

Sources & evidence

ORD record
ord-e5a9dfac1ea547a1b5f31fa98c2193dd
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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