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

HRID 1842344Notes

Reaction equation

HRID 1842344 reaction equation
[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

Participants

8

Reactant 3

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

Product 2

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

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ae7c5140a3fb427aa5227c662d5cb9ad
Source dataset
uspto-grants-2015_02
Patent number
US08946217B2

Reaction notes

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