Chloroiodomethane → HCID 131735156, compound

HRID 931104Notes

Reaction equation

[CH2:1]([Zn]CC)C.ClCI.[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[CH2:17])[N:11]=1.[Cl-].[NH4+]>ClCCl>[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]2([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:1][CH2:17]2)[N:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of diethylzinc (1M in hexane, 2.0 mL, 2.0 mmol) in dichloromethane (3.7 mL) at −4° C. was added chloroiodomethane (714 mg, 4.0 mmol) dissolved in dichloromethane (1 mL) dropwise. The reaction mixture was stirred at 0° C. for 15 minutes. A solution 2-bromo-6-(1-((tert-butyldimethylsilyl)oxy)vinyl)pyridine (200 mg, 0.6 mmol) in dichloromethane (3.0 mL) was added. The reaction mixture was stirred at 0° C. for 2 h. A cold saturated aqueous solution of ammonium chloride was added and the mixture was extracted with dichloromethane. The organics were dried over sodium sulfate and concentrated under reduced pressure. The crude material was purified via flash chromatography (100% heptanes) to afford 2-bromo-6-(1-((tert-butyldimethylsilyl)oxy)cyclopropyl)pyridine (120 mg, 58%). 1H NMR (400 MHz, CDCl3) δ 0.11 (s, 6H), 0.95 (s, 9H), 1.22-1.28 (m, 2H), 1.39-1.45 (m, 2H), 7.23 (dd, 1H), 7.47 (t, 1H), 7.60 (dd, 1H).

Workup

stirringThe reaction mixture was stirred at 0° C. for 2 h
extractionthe mixture was extracted with dichloromethane
dry with materialThe organics were dried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe crude material was purified via flash chromatography (100% heptanes)

Sources & evidence

ORD record: ord-59b0543511f04edc8b028b1e3fdc20ad
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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