Iodoethane → HCID 58268029, compound

HRID 1615974Notes

Reaction equation

HRID 1615974 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]2[CH:6]=[N:7][NH:8][C:9]=2[CH:10]=1.[H-].[Na+].I[CH2:15][CH3:16]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]2[CH:6]=[N:7][N:8]([CH2:15][CH3:16])[C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 247280636-Bromo-1H-indazol-4-amine

Product 1

HCID 58268029HCID 58268029, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-1H-indazol-4-amine (available from Sinova, 300 mg, 1.41 mmol) in THF (7 ml), cooled to 0° C. was added 60% sodium hydride in mineral oil (62 mg, 1.55 mmol) and the reaction was stirred for 15 mins. Iodoethane (0.124 ml, 1.55 mmol) was added and the reaction was stirred overnight. The reaction was quenched with MeOH (1 ml), diluted with water (10 ml), then extracted into ethyl acetate, which was separated and evaporated to dryness. The residue was purified by silica chromatography using 0-100% ethyl acetate in cyclohexane over 80 mins. Pure fractions were evaporated to give the title compound (110 mg).

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe reaction was quenched with MeOH (1 ml)
  3. additiondiluted with water (10 ml)
  4. extractionextracted into ethyl acetate, which
  5. customwas separated
  6. customevaporated to dryness
  7. customThe residue was purified by silica chromatography
  8. customover 80 mins
  9. customPure fractions were evaporated

Sources & evidence

ORD record
ord-c0560a184c814887ba2713b182b13373
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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