Methyl iodide → HCID 67004302, compound

HRID 2095674Notes

Reaction equation

HRID 2095674 reaction equation
[Br:1][C:2]1[C:3]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[N:4][N:5]([CH3:7])[CH:6]=1.[CH2:17]1COCC1.[Li+].CC([N-]C(C)C)C.C1CCCCC1.CI.[NH4+].[Cl-]>>[Br:1][C:2]1[C:3]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:11])[CH3:12])=[N:4][N:5]([CH3:7])[C:6]=1[CH3:17]

Participants

7

Reactant 6

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 8078CyclohexaneHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 67004374HCID 67004374, compound

Product 1

HCID 67004302HCID 67004302, compound

Procedure

A solution of 4-bromo-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-methyl-1H-pyrazole (130.0 mg, 0.4258 mmol) in THF (2 mL, 20 mmol) was cooled to −78° C., and 1.5 M of LDA in cyclohexane (0.85 mL, 1.3 mmol) was added. After stirring for 1 h, methyliodide (0.1 mL, 2 mmol) was added slowly, and the mixture was stirred at −78° C. for 1 h. Sat. NH4Cl was added to quench, and the organic solvent was removed in vacuo. The material was extracted with DCM and water, and the organic layer was concentrated in vacuo to afford the title compound as yellow solid. 1H NMR (400 MHz, CD3OD): δ=0.07 (s, 6H), 0.86 (s, 9H), 2.21 (s, 3H), 3.73 (s, 3H), 4.50 (s, 2H).

Workup

  1. stirringthe mixture was stirred at −78° C. for 1 h
  2. customto quench
  3. customthe organic solvent was removed in vacuo
  4. extractionThe material was extracted with DCM and water
  5. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-6e3cfaaf310d4de9809507420bd8d1f2
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

Loading…