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

HRID 273223Notes

Reaction equation

HRID 273223 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-4c8fe698b66a4bfb8dbcd755d1236f2a
Source dataset
uspto-grants-2008_11
Patent number
US07456196B2

Reaction notes

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