Methyl iodide → 5-Bromo-2-[2-(methylsulfonyl)propan-2-yl]-1,3-thiazole

HRID 1040086ノート

反応式

HRID 1040086 の反応式
[Br:1][C:2]1[S:6][C:5]([C:7]([S:10]([CH2:13]CC(OC)=O)(=[O:12])=[O:11])([CH3:9])[CH3:8])=[N:4][CH:3]=1.C[O-].[Na+].CI>C1COCC1.CS(C)=O.O>[Br:1][C:2]1[S:6][C:5]([C:7]([S:10]([CH3:13])(=[O:11])=[O:12])([CH3:9])[CH3:8])=[N:4][CH:3]=1

参加物

7

反応物 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 67258095Methyl 3-{[2-(5-bromo-1,3-thiazol-2-yl)propan-2-yl]sulfonyl}propanoate

生成物 1

HCID 672585745-Bromo-2-[2-(methylsulfonyl)propan-2-yl]-1,3-thiazole収率 93.3%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl 3-{[2-(5-promo-1,3-thiazol-2-yl)propan-2-yl]sulfonyl}propanoate (Example 70, Step 4, 500 mg, 1.403 mmol) was taken up in THF (15 mL) at room temperature, and NaOMe (25% in MeOH, 303 mg, 1.403 mmol) was added. After 30 min at room temperature, the suspension was evaporated to dryness, providing a white solid. The solid was taken back up in DMSO (5 mL), and methyl iodide (398 mg, 2.81 mmol) was added. After stirring for 2 h at room temperature, the reaction was diluted with water and extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated. Flash chromatography (0-40% ethyl acetate in hexanes) afforded of 5-bromo-2-[2-(methylsulfonyl)propan-2-yl]-1,3-thiazole (372 mg, 93%) as a colorless solid. MS ESI: [M+H]+ m/z 283.9/285.9.

後処理

  1. customthe suspension was evaporated to dryness
  2. customproviding a white solid
  3. extractionextracted with ethyl acetate (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-4e1f2f3564b041f38fecf7a8e6b51b5a
出典データセット
uspto-grants-2013_10
特許番号
US08551984B2

反応ノート

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