Potassium Carbonate → Methyl 3-chloro-3'-((2-cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)biphenyl-4-carboxylate

HRID 404965Notes

Reaction equation

HRID 404965 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]1([N:12]2[C:16](=[O:17])[C:15]3[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:14]=3[S:13]2)[CH2:11][CH2:10][CH2:9][CH2:8]1.Br[CH2:24][C:25]1[CH:26]=[C:27]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([O:39][CH3:40])=[O:38])=[C:33]([Cl:41])[CH:32]=2)[CH:28]=[CH:29][CH:30]=1>CC#N>[Cl:41][C:33]1[CH:32]=[C:31]([C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([CH2:24][O:22][C:20]3[CH:19]=[CH:18][C:15]4[C:16](=[O:17])[N:12]([CH:7]5[CH2:8][CH2:9][CH2:10][CH2:11]5)[S:13][C:14]=4[CH:21]=3)[CH:26]=2)[CH:36]=[CH:35][C:34]=1[C:37]([O:39][CH3:40])=[O:38]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 250674612-cyclopentyl-6-hydroxybenzo[d]isothiazol-3(2H)-oneHCID 66799681Methyl 3'-(bromomethyl)-3-chlorobiphenyl-4-carboxylate

Product 1

HCID 66799479Methyl 3-chloro-3'-((2-cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)biphenyl-4-carboxylateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (0.052 g, 0.38 mmol) was added to a solution of 2-cyclopentyl-6-hydroxybenzo[d]isothiazol-3(2H)-one (0.075 g, 0.32 mmol) and methyl 3′-(bromomethyl)-3-chlorobiphenyl-4-carboxylate (0.129 g, 0.38 mmol) in CH3CN (5 mL). After stirring for 12 h at 80° C., the organic phase was evaporated under reduced pressure and the crude material was partitioned between water and CH2Cl2. The aqueous layer was extracted with CH2Cl2 (3×15 mL). The organic layer was dried over Na2SO4 and evaporated to give methyl 3-chloro-3′-((2-cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)biphenyl-4-carboxylate (0.158 g, quantitative yield). The crude product was used for the next step without further purification. LC-MS (ESI) Calcd for C27H24NO2S [M+H]+: 494.11. Found: 494.00.

Workup

  1. customthe organic phase was evaporated under reduced pressure
  2. customthe crude material was partitioned between water and CH2Cl2
  3. extractionThe aqueous layer was extracted with CH2Cl2 (3×15 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-c93b17da5a4142d7a3cde664a11e8ae1
Source dataset
uspto-grants-2014_06
Patent number
US08748632B2

Reaction notes

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