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HRID522976

反应详情

EQUATION

反应方程式

HRID 522976 的结构方程式

REACTANTS

反应物

3
结构：c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1
HCID634876

2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

C44H32P2

结构：Cc1c(N)cnn1C.Cl.Cl
HCID44630906

1,5-Dimethyl-1H-pyrazol-4-amine--hydrogen chloride (1/2)

C5H11Cl2N3

结构：CC(C)(C)NC(=O)c1cn(COCC[Si](C)(C)C)c2ncc(Br)nc12
HCID71575645

未命名化合物

PRODUCTS

生成物

1
结构：Cc1c(Nc2cnc3c(n2)c(C(=O)NC(C)(C)C)cn3COCC[Si](C)(C)C)cnn1C
HCID90040996

未命名化合物

收率 28%

AUXILIARIES

试剂、催化剂与溶剂

5
结构：CC(=O)[O-].CC(=O)[O-].[Pd+2]
催化剂HCID167845

Diacetatopalladium

C4H6O4Pd

结构：CC(C)(C)[O-].[Na+]
催化剂HCID23676156

Sodium t-butoxide

C4H9NaO

结构：O
溶剂HCID962

Water

H2O

结构：Cc1ccccc1
溶剂HCID1140

Toluene

C7H8

结构：CN(C)C=O
溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度
140 °C

PROCEDURE

实验过程

A mixture of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (150 mg, 351 mol), 1,5-dimethyl-1H-pyrazol-4-amine dihydrochloride (96.9 mg, 526 mol), BINAP (10.9 mg, 17.5 mol), palladium (II) acetate (19.7 mg, 87.7 mol) and sodium tert-butoxide (118 mg, 1.23 mmol) in DMF (1 mL) and toluene (500 L) was heated in a microwave at 140° C. for 20 min. The reaction mixture was diluted with water then extracted into ethyl acetate (3×). The combined organic extracts were washed with brine then dried over magnesium sulfate. Purification by chromatography (50-100% ethyl acetate in hexanes) gave N-tert-butyl-2-(1,5-dimethyl-1H-pyrazol-4-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (45 mg, 98.3 mol, 28%) as a yellow gum. (EI/CI) m/z: 458.3 [M+H].

WORKUP

后处理

  1. extractionthen extracted into ethyl acetate (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialthen dried over magnesium sulfate
  4. customPurification by chromatography (50-100% ethyl acetate in hexanes)