Triethylamine → HCID 57860171, compound

HRID 1947156Notes

Reaction equation

HRID 1947156 reaction equation
[CH3:1][O:2][C:3]1[C:7]2[C:8](=[O:25])[N:9]([CH2:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]=2[N:5]([CH3:26])[C:4]=1[C:27]([NH:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:28].Br[C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][CH:44]=1)[C:40]#[N:41].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC(C)([O-])C.[Na+].C(N(CC)CC)C>CC(=O)CC.O.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]>[C:40]([C:39]1[CH:38]=[C:37]([N:33]2[CH2:32][CH2:31][CH:30]([NH:29][C:27]([C:4]3[N:5]([CH3:26])[C:6]4[C:15]5[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=5[N:9]([CH2:16][C:17](=[O:24])[C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)[C:8](=[O:25])[C:7]=4[C:3]=3[O:2][CH3:1])=[O:28])[CH2:35][CH2:34]2)[CH:44]=[CH:43][CH:42]=1)#[N:41]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 233813-BromobenzonitrileHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 57860479HCID 57860479, compound

Product 1

HCID 57860171HCID 57860171, compoundYield 7.4%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of the compound of Example 77 (300 mg, 0.59 mmol), 3-bromobenzonitrile (143 mg, 1.2 mmol), tris(dibenzylideneacetone)dipalladium (0) (54 mg, 0.059 mmol), x-phos (56 mg, 0.12 mmol), sodium tert-butoxide (142 mg, 1.5 mmol) and triethylamine (0.082 mL, 0.59 mmol) in 2-butanone (4.0 mL) was stirred under microwave irradiation at 130° C. for 40 min. The reaction mixture was diluted with water, and extracted twice with ethyl acetate. The extract was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; ethyl acetate/hexane=40/60-100/0) and recrystallized from ethyl acetate-hexane to give the title compound (25 mg, 7.4%) as a white solid.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe extract was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by aminosilica gel chromatography (eluate; ethyl acetate/hexane=40/60-100/0)
  5. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ddce4c75cdc44a83a161b813f17633e0
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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