Water → HCID 76072045, compound

HRID 927056Notes

Reaction equation

HRID 927056 reaction equation
Br[CH2:2][C:3]1[CH:13]=[CH:12][C:6]2[S:7](=[O:11])(=[O:10])[CH2:8][CH2:9][C:5]=2[CH:4]=1.[NH2:14][C:15]1[C:16]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[N:17][O:18][CH:19]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[O:10]=[S:7]1(=[O:11])[CH2:8][CH2:9][C:5]2[CH:4]=[C:3]([CH2:2][O:26][C:23]3[CH:22]=[CH:21][C:20]([C:16]4[C:15]([NH2:14])=[CH:19][O:18][N:17]=4)=[CH:25][CH:24]=3)[CH:13]=[CH:12][C:6]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 17966545HCID 17966545, compoundHCID 136491269HCID 136491269, compound

Product 1

HCID 76072045HCID 76072045, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromomethyl-2,3-dihydro-benzo[b]thiophene 1,1-dioxide (55 mg, 0.21 mmol), 4-(4-amino-isoxazol-3-yl)-phenol (37 mg, 0.21 mmol) in DMF (2 mL) was added tetrabutylammonium iodide (8 mg, 0.021 mmol) and K2CO3 (58 mg, 0.42 mmol). After stirring for 4 h at rt, the reaction mixture was poured into water and extracted three times with ethyl acetate. The combined organic layers were washed three times with water, once with brine and dried over Na2SO4. Filtration followed by removal of volatiles under reduced pressure gave crude product from which 3-[4-(1,1-dioxo-2,3-dihydro-1H-1lambda*6*-benzo[b]thiophen-5-ylmethoxy)-phenyl]-isoxazol-4-ylamine (42 mg, 56%) was isolated by chromatography (66-80% ethyl acetate in hexane. M+1=356.9

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic layers were washed three times with water
  3. dry with materialonce with brine and dried over Na2SO4
  4. filtrationFiltration
  5. customfollowed by removal of volatiles under reduced pressure

Sources & evidence

ORD record
ord-94e6937778994a6cb29d1c777c290337
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

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