Реакция #325211

ord-dfaa7f9fb08240b5acc19bdf0a98b165

Уравнение реакции

Cn1cc(I)c2c(Cl)ncnc21
4-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidine
OB(O)c1ccc2ccccc2c1
naphthalen-2-yl-2-boronic acid
O=C([O-])[O-].[Na+].[Na+]
Na2CO3
Cn1cc(-c2ccc3ccccc3c2)c2c(Cl)ncnc21
ZK102
Выход 26.2%
Cn1cc(-c2ccc3ccccc3c2)c2c(Cl)ncnc21
4-chloro-7-methyl-5-(naphthalen-2-yl)-7H-pyrrolo[2,3-d]pyrimidine
Выход 26.2%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Температураto reflux overnight under an argon atmosphere
  2. 2
    ДругоеReaction
  3. 3
    Концентрированиеwas concentrated in vacuo
  4. 4
    Другоеpurified by RP-HPLC (MeCN:H2O:0.1% TFA)

Методика

A solution of 4-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (19 mg, 0.065 mmol), naphthalen-2-yl-2-boronic acid (12.2 mg, 0.071 mmol), Na2CO3 (68.9 mg, 0.65 mmol) and PdCl2(dppf) (26.5 mg, 0.00325 mmol) in THF (3 mL) was heated to reflux overnight under an argon atmosphere. Reaction was concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield ZK102 (5 mg, 26% yield). ESI-MS (M+H)+ m/z calcd 294.1, found 294.3.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08642604B2uspto-grants-2014_02