Methyl iodide → 2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole

HRID 1842344노트

반응식

HRID 1842344 반응식
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[N:12][NH:13]3)[O:3]1.[H-].[Na+].I[CH3:22]>CN(C=O)C.C1COCC1.C(Cl)Cl>[CH3:22][N:13]1[C:14]2[C:10](=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:18])([CH3:1])[O:3]3)[CH:17]=[CH:16][CH:15]=2)[CH:11]=[N:12]1.[CH3:22][N:12]1[CH:11]=[C:10]2[C:14]([CH:15]=[CH:16][CH:17]=[C:9]2[B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:18])([CH3:1])[O:3]2)=[N:13]1

참가 물질

8

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole

생성물 2

HCID 441182542-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazoleHCID 454801871-Methyl-1H-indazole-4-boronic acid pinacol ester

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indazole (400 mg) in dry DMF (4 mL) precooled to 0° C. was added to a suspension of sodium hydride (80 mg) in dry THF (5 mL) at −78° C. under inert atmosphere. After 30 min, iodomethane (112 uL) was added to the mixture at −78° C. The reaction mixture was allowed slowly to warm up to room temperature overnight and then diluted with DCM, washed with brine, dried (MgSO4) and the solvent removed in vacuo. The residue was purified using flash chromatography to yield 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indazole (143 mg) and 2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2H-indazole (160 mg).

후처리

  1. customprecooled to 0° C.
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was purified

출처 및 근거

ORD 기록
ord-ae7c5140a3fb427aa5227c662d5cb9ad
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946217B2

반응 노트

불러오는 중…