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Hydrochloric Acid → 1-(3-Bromophenyl)-4-fluoro-1-(4-methoxyphenyl)-1H-isoindol-3-amine

HRID 1662178
ノート
印刷プレビュー

反応式

HRID 1662178 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Mg]Br)=[CH:5][CH:4]=1.[Br:11][C:12]1[CH:13]=[C:14]([C:18]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=2[C:33]#[N:34])=[N:19]S(C(C)(C)C)=O)[CH:15]=[CH:16][CH:17]=1.Cl>C1COCC1>[Br:11][C:12]1[CH:13]=[C:14]([C:18]2([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:26]3[C:27](=[C:28]([F:32])[CH:29]=[CH:30][CH:31]=3)[C:33]([NH2:34])=[N:19]2)[CH:15]=[CH:16][CH:17]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 76821598N-((3-bromophenyl)(2-cyano-3-fluorophenyl)methylene)-2-methylpropane-2-sulfinamideHCID 178491912HCID 178491912、化合物

生成物 1

HCID 585795181-(3-Bromophenyl)-4-fluoro-1-(4-methoxyphenyl)-1H-isoindol-3-amine収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4-Methoxyphenylmagnesium bromide (6.00 mL, 3.00 mmol) was added to a solution of N-((3-bromophenyl)(2-cyano-3-fluorophenyl)methylene)-2-methylpropane-2-sulfinamide (0.407 g, 1 mmol) in THF (10 mL) at 0° C. under an argon atmosphere. The resulting mixture was stirred and allowed to reach r.t. over night, then quenched with saturated aqueous NH4Cl, diluted with saturated aqueous NaHCO3 and extracted with DCM. The combined organics were passed through a phase separator (Sorbent) and concentrated. The residue was dissolved in MeOH (10 mL), and hydrogen chloride (2M in diethyl ether, 2 mL, 4 mmol) was added and the resulting mixture was stirred at r.t for 2.5 h. The mixture was concentrated in vacuo and purified on a silica gel column eluted with 0-5% 0.1M NH3 in MeOH in DCM to afford 0.39 g (95% yield) of the title compound: MS (ES+) m/z 411, 413 [M+1]+.

後処理

  1. waitto reach r.t. over night
  2. customquenched with saturated aqueous NH4Cl
  3. additiondiluted with saturated aqueous NaHCO3
  4. extractionextracted with DCM
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in MeOH (10 mL)
  7. stirringthe resulting mixture was stirred at r.t for 2.5 h
  8. concentrationThe mixture was concentrated in vacuo
  9. custompurified on a silica gel column
  10. washeluted with 0-5% 0.1M NH3 in MeOH in DCM

出典と根拠

ORDレコード
ord-bff5000916b84ab7958787a670396b4a
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08030500B2

反応ノート

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