Formaldehyde → HCID 71089596、化合物

HRID 331031ノート

反応式

HRID 331031 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[C:4]([F:11])[CH:3]=1.[C:12]([BH3-])#N.[Na+].C=O>C(O)(=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH3:12])=[C:4]([F:11])[CH:3]=1

参加物

5

反応物 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 247281696-bromo-4-fluoro-1H-indole

生成物 1

HCID 71089596HCID 71089596、化合物収率 40.6%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a stirred solution of 6-bromo-4-fluoro-1H-indole (412 mg, 1.925 mmol) in acetic acid (10.600 mL) at RT was added sodium cyanoborohydride (605 mg, 9.62 mmol). Reaction mixture was stirred for 15 mins Paraformaldehyde (578 mg, 19.25 mmol) was then added and the reaction mixture was stirred at RT for 4 hours. Reaction mixture was quenched with saturated Na2CO3 aqueous solution (ca. 30 mL) and extracted with DCM (ca. 25 mL twice). The combined organic layers were dried over phase separator and solvent removed in vacuo. The resulting material was purified using chromatography on silica (eluted with 5-10% ethyl acetate/cyclohexane) to afford the title compound (180 mg). LCMS (A): m/z (M+H)+ 230/232, C9H9BrFN requires 229/231 (acidic).

後処理

  1. customReaction mixture
  2. additionwas then added
  3. customReaction mixture
  4. customwas quenched with saturated Na2CO3 aqueous solution (ca. 30 mL)
  5. extractionextracted with DCM (ca. 25 mL twice)
  6. customThe combined organic layers were dried over phase separator and solvent
  7. customremoved in vacuo
  8. customThe resulting material was purified

出典と根拠

ORDレコード
ord-d66126a92fec4e7aad5fd15604d8df7c
出典データセット
uspto-grants-2014_11
特許番号
US08877742B2

反応ノート

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