2,6-Dichloro-4-iodopyridine → HCID 53670219, compound

HRID 2272650Notes

Reaction equation

HRID 2272650 reaction equation
[Br-].[CH:2]1([Zn+])[CH2:4][CH2:3]1.[Cl:6][C:7]1[CH:12]=[C:11](I)[CH:10]=[C:9]([Cl:14])[N:8]=1>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:6][C:7]1[CH:12]=[C:11]([CH:2]2[CH2:4][CH2:3]2)[CH:10]=[C:9]([Cl:14])[N:8]=1

Participants

5

Reactant 2

HCID 117373932,6-Dichloro-4-iodopyridineHCID 178419765HCID 178419765, compound

Product 1

HCID 53670219HCID 53670219, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Cyclopropylzinc bromide (0.5 M in tetrahydrofuran, 15 mL, 7.3 mmol) was added to a mixture of 2,6-dichloro-4-iodopyridine (1.0 g, 3.65 mmol) and tetrakis(triphenylphosphine)palladium(0) (211 mg, 0.182 mmol) in anhydrous tetrahydrofuran (10 mL) at 0° C. After being stirred at room temperature for 4 hours, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether: ethyl acetate=100:1) to provide 2,6-dichloro-4-cyclopropylpyridine. MS ESI calc'd. for C8H8Cl2N [M+H]+ 188. found 188. 1H NMR: (400 MHz, CDCl3) δ 6.89 (s, 2H), 1.87-1.80 (m, 1H), 1.18-1.13 (m, 2H), 0.84-0.80 (m, 2H).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (petroleum ether: ethyl acetate=100:1)

Sources & evidence

ORD record
ord-e5e7370f43a94f6b861e1c1fb9719bab
Source dataset
uspto-grants-2015_09
Patent number
US09120785B2

Reaction notes

Loading…