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

HRID 60909

반응식

HRID 60909 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f9bf1d451c994de585039736b601cfed
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440982B2

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