Water → 2-(7-Bromo-3-isoquinolinyl)ethyl 4-methylbenzenesulfonate

HRID 551541Notes

Reaction equation

HRID 551541 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH2:12][CH2:13][OH:14])[N:8]=[CH:9]2)=[CH:4][CH:3]=1.[S:15](Cl)([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=[O:17])=[O:16].C(N(CC)CC)C.O>CN(C1C=CN=CC=1)C.ClCCl>[CH3:22][C:21]1[CH:23]=[CH:24][C:18]([S:15]([O:14][CH2:13][CH2:12][C:7]2[N:8]=[CH:9][C:10]3[C:5]([CH:6]=2)=[CH:4][CH:3]=[C:2]([Br:1])[CH:11]=3)(=[O:17])=[O:16])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 210439272-(7-Bromo-3-isoquinolinyl)ethanol

Product 1

HCID 865922262-(7-Bromo-3-isoquinolinyl)ethyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The product from Example 52E (0.51 g, 2.0 mmol), tosyl chloride (0.68 g, 3.6 mmol), triethylamine (0.55 g, 5.4 mmol), and DMAP (25 mg, 0.2 mmol) were combined in dichloromethane (20 mL) and stirred at room temperature for 6 hours. The mixture was treated with water (0.5 mL), stirred for 2 hours, and then treated with additional water (15 mL). The organic layer was separated, washed with aqueous sodium chloride solution (10 mL, 10%), evaporated in vacuo, and the residue was azeotroped with heptane (15 mL) to provide the title compound which was used in the next step without further purification.

Workup

  1. stirringstirred for 2 hours
  2. customThe organic layer was separated
  3. washwashed with aqueous sodium chloride solution (10 mL, 10%)
  4. customevaporated in vacuo
  5. customthe residue was azeotroped with heptane (15 mL)

Sources & evidence

ORD record
ord-43575af23dca42359c81398e9d04f98f
Source dataset
uspto-grants-2011_05
Patent number
US07947711B2

Reaction notes

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