Lithium Hexamethyldisilazide → 3-(4-Bromo-6-methyl-1H-indazol-1-yl)benzoic acid

HRID 1925592ノート

反応式

HRID 1925592 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4](Br)[C:3]=1[CH:10]=[N:11][NH:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([OH:18])=[O:17].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]2[C:3]=1[CH:10]=[N:11][N:12]2[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([OH:18])=[O:17]

参加物

4

反応物 2

HCID 2733832Lithium HexamethyldisilazideHCID 671571683-{2-[(2,6-Dibromo-4-methylphenyl)methylidene]hydrazino}benzoic acid

生成物 1

HCID 576726453-(4-Bromo-6-methyl-1H-indazol-1-yl)benzoic acid収率 88%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A solution of 3-{2-[(2,6-dibromo-4-methylphenyl)methylidene]hydrazino}benzoic acid (1050 g) in DMF (3.46 L) was cooled to 10° C. under nitrogen. Lithium bis(trimethylsilyl)amide solution (1M in THF, 6.34 L) was then added while maintaining the temperature below 15° C. The stirred solution was heated at 70±3° C. for 64 hrs and then the reaction mixture was cooled to 5° C. and quenched sequentially with the slow addition of water (4.2 L), 5M hydrochloric acid (2.62 L) and water (3.68 L). The resulting slurry was stirred at 5° C. for 1 hr 34 min, filtered and washed successively with purified water (1 L and then 2.1 L at 5±5° C.) and methanol (2×1 L at 5±5° C.). The solid was dried in vacuo at 50° C. to afford the title compound (742.9 g).

後処理

  1. temperaturewhile maintaining the temperature below 15° C
  2. temperaturethe reaction mixture was cooled to 5° C.
  3. customquenched sequentially with the slow addition of water (4.2 L), 5M hydrochloric acid (2.62 L) and water (3.68 L)
  4. filtrationfiltered
  5. washwashed successively with purified water (1 L
  6. customat 5±5° C.
  7. custommethanol (2×1 L at 5±5° C.)
  8. customThe solid was dried in vacuo at 50° C.

出典と根拠

ORDレコード
ord-26cdd1dc04644fc4880c2bb7d1310145
出典データセット
uspto-grants-2012_05
特許番号
US08178573B2

反応ノート

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