Benzenesulfonyl chloride → HCID 44325352, compound

HRID 397104Notes

Reaction equation

HRID 397104 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)[CH2:8][NH:9][CH2:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:28]1([S:34](Cl)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.B(Br)(Br)Br>C(Cl)Cl>[C:28]1([S:34]([N:9]2[CH2:8][CH:7]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[C:6]3[C:11](=[CH:12][C:3]([OH:2])=[CH:4][CH:5]=3)[CH2:10]2)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 25134Boron tribromideHCID 18172424HCID 18172424, compound

Product 1

HCID 44325352HCID 44325352, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7-methoxy-4-(4-methoxy-phenyl)-1,2,3,4-tetrahydroisoquinoline (0.103 g, 0.382 mmol, 1.0 eq., see Preparation 64) and triethylamine (0.107 ml, 0.764 mmol, 2.0 eq.) in CH2Cl2 (2 ml) was added to a vial containing benzenesulfonyl chloride (0.101 g, 0.573 mmol, 1.5 eq.). The reaction mixture was stirred overnight at RT. To this mixture was added BBr3 as a 1.0M solution in CH2Cl2 (1.15 ml, 1.15 mmol, 3.0 eq.). The reaction mixture was again stirred overnight at RT, then cooled to −78° C. and quenched with MeOH (1.5 ml). The reaction mixture was evaporated under a stream of nitrogen and purified by reverse phase HPLC (gradient elution 98:2 H2O:0.1% TFA, then 2:98 MeCN:H2O). The exact yield was not determined.

Workup

  1. waitThe reaction mixture was again stirred overnight at RT
  2. temperaturecooled to −78° C.
  3. customquenched with MeOH (1.5 ml)
  4. customThe reaction mixture was evaporated under a stream of nitrogen
  5. custompurified by reverse phase HPLC (
  6. washgradient elution 98:2 H2O
  7. customThe exact yield

Sources & evidence

ORD record
ord-be0c42987eb1408d91bc33e38dcebd2c
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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