Water → HCID 15838486, compound

HRID 342026Notes

Reaction equation

HRID 342026 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.[H-].[Na+].[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.O>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:26]([C:23]1[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=1)(=[O:28])=[O:27])[CH:6]=[C:5]2[CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 158384855-bromo-3-(2-(pyrrolidin-1-yl)ethyl)-1H-indole

Product 1

HCID 15838486HCID 15838486, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-3-(2-pyrrolidinylethyl)-1H-indole (Example 2, 9.10 g, 31 mmol) in tetrahydrofuran (100 mL) cooled to 0° C., were added sodium hydride (12.4 g, 310 mmol) and p-toluenesulfonyl chloride (6.10 g, 32 mmol). The resulting mixture was stirred at room temperature for 3 h, poured into water (200 mL) and extracted into ethyl acetate (200 mL). The organic phase was washed with water (200 mL) and then poured onto a silica gel column which was eluted with ethyl acetate followed by methanol. The title compound was obtained as a yellow syrup (11.7 g, 90%).

Workup

  1. extractionextracted into ethyl acetate (200 mL)
  2. washThe organic phase was washed with water (200 mL)
  3. additionpoured onto a silica gel column which
  4. washwas eluted with ethyl acetate

Sources & evidence

ORD record
ord-18dc730b549a4402abb2aa7a12f278c5
Source dataset
uspto-grants-1999_01
Patent number
US05856510

Reaction notes

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