2,5-Dibromopyridine → HCID 69069498, compound

HRID 1916719Notes

Reaction equation

HRID 1916719 reaction equation
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)[C:2]#[CH:3].Br[C:20]1[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][N:21]=1>C1COCC1.C(NC(C)C)(C)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:26][C:23]1[CH:24]=[CH:25][C:20]([C:3]#[C:2][CH2:1][N:4]2[C:12]3[C:7](=[CH:8][C:9]([CH2:13][N:14]4[CH2:15][CH2:16][CH2:17][CH2:18]4)=[CH:10][CH:11]=3)[CH:6]=[CH:5]2)=[N:21][CH:22]=1

Participants

7

Reactant 2

HCID 693532,5-DibromopyridineHCID 85969576HCID 85969576, compound

Product 1

HCID 69069498HCID 69069498, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 7912DiisopropylamineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere 5 mg (0.03 mmol) CuI and 18 mg (0.03 mmol) Pd(PPh3)2Cl2 are added to a solution of 337 mg (1.41 mmol) 1-prop-2-ynyl-5-pyrrolidin-1-ylmethyl-1H-indole and 345 mg (1.41 mmol) 2,5-dibromo-pyridine in 50 mL THF and 0.4 mL diisopropylamine and the reaction mixture is stirred for 17 h at RT. The mixture is evaporated down i. vac., the residue is taken up in 30 mL EtOAc, the organic phase is washed with 30 mL water and 30 mL saturated NaCl solution and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, EtOAc/MeOH/NH3 95:5:0.5).

Workup

  1. customThe mixture is evaporated down i
  2. washthe organic phase is washed with 30 mL water and 30 mL saturated NaCl solution
  3. dry with materialdried over Na2SO4
  4. customis purified by chromatography (silica gel, EtOAc/MeOH/NH3 95:5:0.5)

Sources & evidence

ORD record
ord-ca68a867b2ca4dceb9377ee75c440870
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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