Water → 6-bromo-2-(2-fluorobenzyl)-2H-indazol-3-amine

HRID 1973009ノート

反応式

HRID 1973009 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4](F)[CH:3]=1.C(NC(C)C)(C)C.Cl.Cl.[F:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[CH2:23][NH:24][NH2:25].O>C(O)CCC.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:8]([CH:9]=1)=[N:25][N:24]([CH2:23][C:22]1[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=1[F:20])[C:6]=2[NH2:7]

参加物

7

反応物 4

HCID 962WaterHCID 7912DiisopropylamineHCID 7360294-Bromo-2-fluorobenzonitrileHCID 56604647(2-Fluorobenzyl)hydrazine dihydrochloride

生成物 1

HCID 585296596-bromo-2-(2-fluorobenzyl)-2H-indazol-3-amine収率 31%

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
125 °C

実験手順

To a solution of 4-bromo-2-fluorobenzonitrile (3.19 g, 15.64 mmol) and diisopropylamine (13.16 mL, 93.86 mmol) in n-butanol (70 mL) was added (2-fluorobenzyl)hydrazine dihydrochloride (10 g, 46.93 mmol) and the very thick slurry was heated to 125° C. (the mixture became a cloudy solution at 90° C.) for 18 h. The reaction mixture was poured into water and ethyl acetate. The organic layer was isolated and washed with brine, dried over Na2SO4 and concentrated. The resulting light brown solid was taken up in DCM (60 mL) and the suspension stirred for 15 min and filtered. The filter cake was washed with very little DCM and hexanes and dried on a high vacuum pump to give the product as a light brown solid (1.55 g, 31%). LC-MS [M+H]+=320.3, 322.3, RT=2.33 min.

後処理

  1. customat 90° C.
  2. customfor 18 h
  3. customThe organic layer was isolated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. filtrationfiltered
  8. washThe filter cake was washed with very little DCM and hexanes
  9. customdried on a high vacuum pump

出典と根拠

ORDレコード
ord-81b19fa6b46d4c0c8e49a08ddfeb5141
出典データセット
uspto-grants-2013_04
特許番号
US08431695B2

反応ノート

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