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Bicarbonate Ion → 5-Fluoro-1-methanesulphonyl-6-methoxyindole

HRID 23949
Notes
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Reaction equation

HRID 23949 reaction equation
CO[CH:3](OC)[CH2:4][N:5]([S:15]([CH3:18])(=[O:17])=[O:16])[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([O:13][CH3:14])[CH:7]=1.C(=O)(O)[O-]>C1(C)C=CC=CC=1.Cl[Ti](Cl)(Cl)Cl>[F:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:13][CH3:14])[N:5]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:4]=[CH:3]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 769Bicarbonate IonHCID 22570034N-(2,2-dimethoxyethyl)-N-methanesulphonyl-4-fluoro-3-methoxyaniline

Product 1

HCID 225700505-Fluoro-1-methanesulphonyl-6-methoxyindole

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of N-(2,2-dimethoxyethyl)-N-methanesulphonyl-4-fluoro-3-methoxyaniline (1.91 g, 0.65 mmol) in dry toluene at 0° C. under argon, was added slowly a solution of TiCl4 (0.173 g, 0.911 mmol) in dry toluene (10 ml). The solution was then heated to 70° C. for 1 h. cooled and poured onto ice/sat. sod. bicarbonate solution (20 ml). The organic layer was separated, washed with sat. sod. bicarbonate solution, 0.5% hydrochloric acid (2×20 ml) and water (2×20 ml). The solution was dried (MgSO4) and evaporated in vacuo to give 5-fluoro-1-methanesulphonyl-6-methoxyindole ((0.102 g)

Workup

  1. temperaturecooled
  2. additionpoured onto ice/
  3. customThe organic layer was separated
  4. washwashed with sat. sod
  5. dry with materialThe solution was dried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-ab5cf9bb3daa461ab50b0a25299f6c60
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06855715B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes