(1-Iodocyclopropyl)(phenyl)sulfane → 2-[4-(1-Phenylsulfanyl-cyclopropoxy)-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid

HRID 2094752Notes

Reaction equation

HRID 2094752 reaction equation
C[O:2][C:3]([C:5]1([NH:14][C:15](=[O:33])[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:23][CH2:24][CH2:25][C:26]3[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=3)[CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].I[C:35]1([S:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:37][CH2:36]1>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[C:39]1([S:38][C:35]2([O:22][C:19]3[CH:20]=[CH:21][C:16]([C:15]([NH:14][C:5]4([C:3]([OH:2])=[O:4])[CH2:13][C:12]5[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=5)[CH2:6]4)=[O:33])=[CH:17][C:18]=3[O:23][CH2:24][CH2:25][C:26]3[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=3)[CH2:37][CH2:36]2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 2

HCID 11000298(1-Iodocyclopropyl)(phenyl)sulfaneHCID 670762682-[4-Hydroxy-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid methyl ester

Product 1

HCID 670763202-[4-(1-Phenylsulfanyl-cyclopropoxy)-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acidYield 65.4%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

The compound of step 1 of example 254 (50 mg, 0.116 mmol), (1-iodo-cyclopropylsulfanyl)-benzene (G. J. Hollingworth et al., Tetrahedron Lett. 40 (1999), 2633-2636) (64 mg, 0.232 mmol) and silver carbonate (64 mg, 0.232 mmol) in toluene (1 ml) were stirred overnight at 50° C. The mixture was filtered, the filtrate evaporated to dryness and the residue purified by silica gel chromatography (HEP/EA gradient) to yield 44 mg of the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated to dryness
  3. customthe residue purified by silica gel chromatography (HEP/EA gradient)

Sources & evidence

ORD record
ord-9bf48d5eadf04a7aa1da99243bbb2fa7
Source dataset
uspto-grants-2013_05
Patent number
US08445530B2

Reaction notes

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