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HRID78721

反应详情

EQUATION

反应方程式

HRID 78721 的结构方程式

REACTANTS

反应物

4
结构：O
HCID962

Water

H2O

结构：O=C([O-])[O-].[Na+].[Na+]
HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

结构：Cc1ccsc1-c1nnc(-c2nc(Br)cnc2N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)o1
HCID59472351

未命名化合物

结构：CC(C)(C)OC(=O)N1CCCC(S(=O)(=O)c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)C1
HCID86682773

未命名化合物

PRODUCTS

生成物

1
结构：Cc1ccsc1-c1nnc(-c2nc(-c3ccc(S(=O)(=O)C4CCCN(C(=O)OC(C)(C)C)C4)cc3)cnc2NC(=O)OC(C)(C)C)o1
HCID86682778

未命名化合物

收率 106.2%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CC#N
溶剂HCID6342

Acetonitrile

C2H3N

CONDITIONS

反应条件

温度
65 °C

PROCEDURE

实验过程

tert-butyl-N-[5-bromo-3-[5-(3-methyl-2-thienyl)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate (750 mg, 1.393 mmol) and tert-butyl 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]sulfonylpiperidine-1-carboxylate (691.5 mg, 1.532 mmol) were suspended in MeCN (7.500 mL)/water (7.500 mL) and Na2CO3 (1.393 mL of 2 M, 2.786 mmol) was added. The reaction mixture was degassed with 3× nitrogen/vacuum cycles. Pd(tBu3P)2 (71.19 mg, 0.1393 mmol) was added and the reaction mixture again degassed 3 times then heated to 65° C. (Dry Syn Temp) for 1.5 hours. The reaction mixture was cooled to ambient temperature and diluted with ethylacetate/water. The aqueous layer was extracted with ethylacetate (×1) and the combined organic extracts washed with brine (×2), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion, 80 g column, eluting with 0 to 30% ethyl acetate/petroleum Ether, (loaded in DCM) to give the sub-title product as a yellow solid (1.01 g, 93% Yield). H NMR (400.0 MHz, DMSO-d6) δ 9.62 (s, 1H), 8.59 (d, 2H), 8.16 (d, 2H), 7.96 (d, 1H), 7.24 (d, 1H), 4.14-3.92 (m, 1H), 3.77 (br d, 1H), 3.44 (br s, 1H), 3.02-2.91 (m, 1H), 2.79 (br t, 1H), 2.67 (s, 3H), 2.05 (br s, 1H), 1.76-1.58 (m, 2H) and 1.35-1.22 (m, 28H) ppm; LC/MS m/z 627 [M−100−56]+.

WORKUP

后处理

  1. additionwas added
  2. customThe reaction mixture was degassed with 3× nitrogen/vacuum cycles
  3. customthe reaction mixture again degassed 3 times
  4. custom(Dry Syn Temp) for 1.5 hours
  5. temperatureThe reaction mixture was cooled to ambient temperature
  6. additiondiluted with ethylacetate/water
  7. extractionThe aqueous layer was extracted with ethylacetate (×1)
  8. washthe combined organic extracts washed with brine (×2)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by column chromatography (ISCO Companion, 80 g column
  13. washeluting with 0 to 30% ethyl acetate/petroleum Ether, (loaded in DCM)