(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮 → 4-t-Butoxy-2,3,6-trifluoro-5-methoxypyridine

HRID 1875

反应方程式

HRID 1875 反应方程式
[C:1]([O:5][C:6]1[C:11]([OH:12])=[C:10]([F:13])[N:9]=[C:8]([F:14])[C:7]=1[F:15])([CH3:4])([CH3:3])[CH3:2].[C:16]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6]1[C:11]([O:12][CH3:16])=[C:10]([F:13])[N:9]=[C:8]([F:14])[C:7]=1[F:15])([CH3:4])([CH3:2])[CH3:3]

参与物

6

反应物 4

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮HCID 11776三苯基膦HCID 5462977偶氮二甲酸二乙酯HCID 106565874-t-Butoxy-2,3,6-trifluoro-5-hydroxypyridine

产物 1

HCID 104899104-t-Butoxy-2,3,6-trifluoro-5-methoxypyridine收率 85.7%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

To a solution of 237 mg (1.07 mmol) of 4-t-butoxy-2,3,6-trifluoro-5-hydroxypyridine, from step 275a above, in 3 mL of anhydrous THF was added 335 mg (1.277 mmol) of triphenyl phosphine and 0.060 mL (1.48 mmol) of methanol. To this solution was added 0.200 mL (1.270 mmol) of DEAD dropwise at room temperature. The reaction was complete in 10 min, so the solvents were removed under vacuum and the residue was purified by flash chromatography on silica gel, eluting with 1:16 ethyl acetate:hexane to give 215.6 mg of the title product as a colorless liquid after removal of the solvent.

后处理

  1. customwere removed under vacuum
  2. customthe residue was purified by flash chromatography on silica gel
  3. washeluting with 1:16 ethyl acetate

来源与证据

ORD记录
ord-60ba32da8a3a420db576adcfd7bcef8c
来源数据集
uspto-grants-1998_03
专利号
US05726182

关联笔记

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