Water → 4-(benzyloxy)-7-bromo-5-fluoro-1-methyl-1H-indole

HRID 1404135Notes

Reaction equation

HRID 1404135 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([F:18])=[CH:16][C:15]([Br:19])=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[CH3:22]I.O>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:17]([F:18])=[CH:16][C:15]([Br:19])=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH3:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 583038564-(benzyloxy)-7-bromo-5-fluoro-1H-indole

Product 1

HCID 583039584-(benzyloxy)-7-bromo-5-fluoro-1-methyl-1H-indoleYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 17-1 (9 g, 28 mmol), potassium hydroxide (2.36 g, 42 mmol) and methyl iodide (6 g, 42 mmol) in DMF (30 mL) was stirred at room temperature for 2 h. The mixture was poured into water (50 mL), extracted with ethyl acetate (3×50 mL). The extracts were washed with water (3×50 mL) and brine (2×50 mL), dried over MgSO4, filtered, and evaporated to afford 33-3 (8 g, 90%) which was used directly in next step. LRMS: calc 333.0 and found: 334.0 [M+1].

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe extracts were washed with water (3×50 mL) and brine (2×50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-3cde77fdedc24c6e8f26156c5430cbdf
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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