3-Chloromethyl-2-cyclobutylsulfanyl-pyridine → [6-(2-Cyclobutylsulfanyl-pyridin-3-ylmethoxy)-5,7-difluoro-2,3-dihydro-benzofuran-3-yl]-acetic acid

HRID 62983Notes

Reaction equation

HRID 62983 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:9][CH:10]2[CH2:13][CH2:12][CH2:11]2)=[N:5][CH:6]=[CH:7][CH:8]=1.C[O:15][C:16](=[O:30])[CH2:17][CH:18]1[C:22]2[CH:23]=[C:24]([F:29])[C:25]([OH:28])=[C:26]([F:27])[C:21]=2[O:20][CH2:19]1>>[CH:10]1([S:9][C:4]2[C:3]([CH2:2][O:28][C:25]3[C:24]([F:29])=[CH:23][C:22]4[CH:18]([CH2:17][C:16]([OH:30])=[O:15])[CH2:19][O:20][C:21]=4[C:26]=3[F:27])=[CH:8][CH:7]=[CH:6][N:5]=2)[CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 901182633-Chloromethyl-2-cyclobutylsulfanyl-pyridineHCID 90118284(5,7-Difluoro-6-hydroxy-2,3-dihydro-benzofuran-3-yl)-acetic acid methyl ester

Product 1

HCID 74221668[6-(2-Cyclobutylsulfanyl-pyridin-3-ylmethoxy)-5,7-difluoro-2,3-dihydro-benzofuran-3-yl]-acetic acidYield 79.8%

Procedure

3-Chloromethyl-2-cyclobutylsulfanyl-pyridine (18 mg, 0.08 mmol) obtained in Step C of Preparation Example 23 and (5,7-difluoro-6-hydroxy-2,3-dihydro-benzofuran-3-yl)-acetic acid methyl ester (20 mg, 0.08 mmol) obtained in Preparation Example 51 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (26 mg, 78%).

Workup

  1. customobtained in Preparation Example 51
  2. customto react sequentially in the same manner as in Steps A and B of Example 1

Sources & evidence

ORD record
ord-84e35ce28fe74b3fbac06cf1eedef383
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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