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

HRID 2353160ノート

反応式

HRID 2353160 の反応式
[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

参加物

8

反応物 3

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

生成物 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

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-77ae0d3b29fc4982b73e4c2cec792cb0
出典データセット
uspto-grants-2010_07
特許番号
US07750002B2

反応ノート

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