Methyl iodide → Ethyl 2-(methylthio)thiazolo[4,5-b]pyridine-6-carboxylate

HRID 1848103ノート

反応式

HRID 1848103 の反応式
[K].[SH:2][C:3]1[S:4][C:5]2[C:6]([N:16]=1)=[N:7][CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=2.I[CH3:18]>CN(C=O)C>[CH3:18][S:2][C:3]1[S:4][C:5]2[C:6]([N:16]=1)=[N:7][CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=2

参加物

4

反応物 2

HCID 6328Methyl iodideHCID 178469699HCID 178469699、化合物

生成物 1

HCID 86681077Ethyl 2-(methylthio)thiazolo[4,5-b]pyridine-6-carboxylate収率 82%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a stirred mixture of ethyl 2-mercaptothiazolo[4,5-b]pyridine-6-carboxylate potassium salt (1.7 g, 6.6 mmol) from the previous step in DMF (10 mL) at 0° C. was added iodomethane (226 μL, 3.6 mmol). After the mixture was stirred at 0° C. for 2 h, it was allowed to warm slowly to rt. The mixture was partitioned between EtOAc (100 mL) and 0.5 M aq Na2CO3 (50 mL). The organic layer was separated and washed with brine (50 mL), dried over Mg2SO4, filtered, and concentrated under reduced pressure to afford ethyl 2-(methylthio)thiazolo[4,5-b]pyridine-6-carboxylate (724 mg, 82%) as a yellow solid. The material was used in the next step without further purification. 1H NMR (300 MHz, DMSO-d6) δ 9.07 (s, 2H), 4.38 (q, J=7.0 Hz, 2H), 2.86 (s, 3H), 1.36 (t, J=7.1 Hz, 3H); LCMS (ESI) m/z 255 (M+H)+.

後処理

  1. temperatureto warm slowly to rt
  2. customThe mixture was partitioned between EtOAc (100 mL) and 0.5 M aq Na2CO3 (50 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (50 mL)
  5. dry with materialdried over Mg2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-5794925101be4877a64e786ce04ea489
出典データセット
uspto-grants-2015_02
特許番号
US08952058B2

反応ノート

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