2-Bromopyridine → HCID 57860593, compound

HRID 1947154Notes

Reaction equation

HRID 1947154 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].I[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=1.C(=O)([O-])[O-].[K+].[K+].BrC1C=CC=CN=1.C(N(CC)CC)C>CN(C=O)C.O>[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[CH2:31][CH2:32][N:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=2)[CH2:34][CH2:35]1)=[O:28]

Participants

8

Reactant 5

HCID 79732-BromopyridineHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 2211262-IodopyridineHCID 57860479HCID 57860479, compound

Product 1

HCID 57860593HCID 57860593, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of the compound of Example 77 (284 mg, 0.60 mmol), 2-iodopyridine (0.13 mL, 1.2 mmol) and potassium carbonate (208 mg, 1.5 mmol) in DMF (3.0 mL) was stirred at 90° C. for 5.5 hr. 2-Bromopyridine (0.23 mL, 2.5 mmol) and triethylamine (0.49 mL, 3.5 mmol) were added to the reaction mixture, and the mixture was stirred under microwave irradiation at 165° for 1 hr. The reaction mixture was diluted with water, and extracted twice with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; ethyl acetate/hexane=30/70-100/0) and recrystallized from THF-diethyl ether to give the title compound (38 mg, 12%) as a white solid.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by aminosilica gel chromatography (eluate; ethyl acetate/hexane=30/70-100/0)
  6. customrecrystallized from THF-diethyl ether

Sources & evidence

ORD record
ord-c74d56ed40a2455293128ee196b6106d
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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