Cesium carbonate → 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

HRID 60909

反応式

HRID 60909 の反応式
Br[C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH:12]1[CH:16]=[CH:15][N:14]=[N:13]1.CN[C@H]1CCCC[C@@H]1NC.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cu]I>[CH3:11][C:8]1[CH:9]=[CH:10][C:2]([N:13]2[N:14]=[CH:15][CH:16]=[N:12]2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 2280802-Bromo-5-methylbenzoic acidHCID 13822957(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamineHCID 178418936HCID 178418936、化合物

生成物 1

HCID 532601655-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid収率 79.4%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

A mixture of 2-bromo-5-methylbenzoic acid (2.0 g, 9.30 mmol), 1,2,3-triazole (1.08 mL, 18.6 mmol), (1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine (2.23 mL, 13.95 mmol), Cs2CO3 (4.55 g, 13.95 mmol) and CuI (124 mg, 0.65 mmol) in DMF (12 mL) was degassed and heated at 120° C. for 1 h in a microwave reactor. The reaction was cooled to rt, diluted with MeOH, and acidified with AcOH to pH 4-5. The solvent was removed in vacuo to obtain the crude which was purified by silica gel chromatography (0˜100% DCM/EtOAc) to yield the title compound as a yellow oil (1.5 g, 61%). MS (ESI) 204 (M+H).

後処理

  1. customwas degassed
  2. temperatureThe reaction was cooled to rt
  3. additiondiluted with MeOH
  4. customThe solvent was removed in vacuo
  5. customto obtain the crude which
  6. customwas purified by silica gel chromatography (0˜100% DCM/EtOAc)

出典と根拠

ORDレコード
ord-f9bf1d451c994de585039736b601cfed
出典データセット
uspto-grants-2016_09
特許番号
US09440982B2

関連ノート

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