Nitrogen → HCID 86648960, compound

HRID 449919

Reaction equation

HRID 449919 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:19])[C:10]2[C:15]([Cl:16])=[CH:14][C:13](I)=[CH:12][C:11]=2[Cl:18])[CH:5]=[CH:4][N:3]=1.[CH3:20][C:21]1(C)C(C)(C)OB(C=C)O1.C([O-])([O-])=O.[Na+].[Na+].N#N>C1COCC1.O>[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:19])[C:10]2[C:15]([Cl:16])=[CH:14][C:13]([CH:20]=[CH2:21])=[CH:12][C:11]=2[Cl:18])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86648959N-(2-bromopyridin-4-yl)-2,6-dichloro-4-iodobenzamide

Product 1

HCID 86648960HCID 86648960, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-(2-bromopyridin-4-yl)-2,6-dichloro-4-iodobenzamide (3.0 g, 6.4 mmol) in THF (40 mL) was added 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (2.0 g, 12.8 mmol), 2M Na2CO3 (12 ml) and Pd2(PPh3)4 (222 mg, 0.19 mmol). The solution was degrassed with N2, and heated at 80° C. overnight. Then the reaction mixture was cooled to room temperature, poured into water (200 mL), and extracted with EtOAc (3×100 mL). The combined organic extracts were washed with brine (2×20 mL), dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica-gel chromatography (Pet Ether/EtOAc=10:1 to 3:1) to give N-(2-bromopyridin-4-yl)-2,6-dichloro-4-vinylbenzamide (2.2 g, yield: 92%). 1H NMR (500 MHz, CDCl3): δ 8.27 (d, J=5.0 Hz, 1H), 8.11 (s, 1H), 7.88 (s, 1H), 7.51 (d, J=3.5 Hz, 1H), 7.35 (s, 2H), 6.61 (m, 1H), 5.86 (d, J=17.5 Hz, 1H), 5.48 (d, J=11.0 Hz, 1H). LCMS (ESI) m/z: 371.0 [M+H+].

Workup

  1. temperatureThen the reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organic extracts were washed with brine (2×20 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica-gel chromatography (Pet Ether/EtOAc=10:1 to 3:1)

Sources & evidence

ORD record
ord-7573dda5f6034898b6d46b23cc6a99b7
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Linked notes

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