Methyl iodide → tert-Butyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate

HRID 57531

반응식

HRID 57531 반응식
[CH3:1][C:2]1([CH3:23])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:11][CH:10]=2)[O:3]1.[H-].[Na+].[CH3:26]I>C1COCC1>[CH3:26][N:15]([C:12]1[CH:13]=[CH:14][C:9]([B:4]2[O:3][C:2]([CH3:23])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:10][CH:11]=1)[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2734617tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate

생성물 1

HCID 4712653tert-Butyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Under N2, to a solution of tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (500 mg, 1.57 mmol) in anhydrous THF (4 mL), was slowly added sodium hydride (94 mg, 2.35 mmol) at 0° C. The mixture was stirred at room temperature for 20 minutes, then cooled to 0° C. CH3I (445 mg, 3.13 mmol) was slowly added. After the completion of the addition, the reaction mixture was stirred at room temperature overnight, quenched with H2O, and extracted with EtOAc. The combined extracts were concentrated, and the residue was purified by flash chromatography to give the title compound. MS (m/z): 278 (M−56)+.

후처리

  1. customat 0° C
  2. temperaturecooled to 0° C
  3. additionAfter the completion of the addition
  4. stirringthe reaction mixture was stirred at room temperature overnight
  5. customquenched with H2O
  6. extractionextracted with EtOAc
  7. concentrationThe combined extracts were concentrated
  8. customthe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-823a12630f8c482c98f23fa1a99513b2
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434726B2

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