تفاعل #423770

ord-1ff4b3e44251469c9cb96c31867c8b6e

معادلة التفاعل

Cc1c(I)ccnc1F
2-fluoro-4-iodo-3-methylpyridine
OCC12CC3CC(CC(C3)C1)C2
1-Hydroxylmethyladamantane
[H-].[Na+]
NaH
Cc1c(I)ccnc1OCC12CC3CC(CC(C3)C1)C2
title compound
Cc1c(I)ccnc1OCC12CC3CC(CC(C3)C1)C2
2-(tricyclo[3.3.1.13,7]dec-1-ylmethoxy)-4-iodo-3-methyl-pyridine

الكواشف

لا شيء

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىquenched with H2O
  2. 2
    استخلاصextracted with ethyl acetate
  3. 3
    غسيلThe combined organic layers were washed with brine
  4. 4
    تركيزconcentrated
  5. 5
    أخرىThe residue was purified by preparative TLC
  6. 6
    غسيلeluting with petroleum ether

الإجراء التجريبي

1-Hydroxylmethyladamantane (249 mg) was dissolved in tetrahydrofuran (3.5 mL) and NaH (24 mg) was added. After the gas evolution ceased, 2-fluoro-4-iodo-3-methylpyridine (237 mg) in tetrahydrofuran (1.5 mL) was added. The reaction mixture was stirred at room temperature for 0.5 hours, quenched with H2O and extracted with ethyl acetate. The combined organic layers were washed with brine and concentrated. The residue was purified by preparative TLC, eluting with petroleum ether to provide the title compound.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08889675B2uspto-grants-2014_11