Boron trifluoride etherate → N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[3,4-(methylenedioxy)benzyl]thieno[2,3-b]pyridine-3-sulfonamide

HRID 1265017Notes

Reaction equation

HRID 1265017 reaction equation
[Cl:1][C:2]1[C:3]([CH3:37])=[N:4][O:5][C:6]=1[N:7]([CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[S:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[S:13][C:12]=1[CH:20](O)[C:21]1[CH:26]=[CH:25][C:24]2[O:27][CH2:28][O:29][C:23]=2[CH:22]=1)(=[O:10])=[O:9].C([SiH](CC)CC)C.B(F)(F)F.CCOCC>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[C:3]([CH3:37])=[N:4][O:5][C:6]=1[N:7]([CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[S:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[S:13][C:12]=1[CH2:20][C:21]1[CH:26]=[CH:25][C:24]2[O:27][CH2:28][O:29][C:23]=2[CH:22]=1)(=[O:9])=[O:10]

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 54238526N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-(alpha-hydroxy-3,4-(methylenedioxy) benzyl]-thieno [2,3-b]pyridine-3-sulfonamide

Product 1

HCID 18614044N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[3,4-(methylenedioxy)benzyl]thieno[2,3-b]pyridine-3-sulfonamideYield 66.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2 -(α-hydroxy-3,4-(methylenedioxy) benzyl]-thieno [2,3-b]pyridine-3-sulfonamide (0.10 g, 0.18 mmoles)[see Example 4(B)] and triethylsilane (0.29 ml, 1.8 mmoles) in CH2Cl2 (2 ml) was added boron trifluoride etherate (0.10 ml, 0.81 mmoles). The orange-brown solution was stirred 2 hours at ambient temperature then diluted with EtOAc (50 ml) and washed with H2O (75 ml). The organic layer was dried (MgSO4), filtered and concentrated to collect an orange oil. Flash chromatography (40% EtOAc/hexanes) provided 66 mg (66%) of the title compound as a yellow oil.

Workup

  1. washwashed with H2O (75 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto collect an orange oil

Sources & evidence

ORD record
ord-b507eaadc994479780a2b757437432a7
Source dataset
uspto-grants-2003_04
Patent number
US06545014B2

Reaction notes

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