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

HRID 62994Notes

Reaction equation

HRID 62994 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:5][CH:6]=[CH:7][CH:8]=1.C[O:16][C:17](=[O:31])[CH2:18][CH:19]1[C:23]2[CH:24]=[C:25]([F:30])[C:26]([OH:29])=[C:27]([F:28])[C:22]=2[O:21][CH2:20]1>>[CH:10]1([S:9][C:4]2[C:3]([CH2:2][O:29][C:26]3[C:25]([F:30])=[CH:24][C:23]4[CH:19]([CH2:18][C:17]([OH:31])=[O:16])[CH2:20][O:21][C:22]=4[C:27]=3[F:28])=[CH:8][CH:7]=[CH:6][N:5]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 901182833-Chloromethyl-2-cyclopentylsulfanyl-pyridineHCID 90118284(5,7-Difluoro-6-hydroxy-2,3-dihydro-benzofuran-3-yl)-acetic acid methyl ester

Product 1

HCID 74221760[6-(2-Cyclopentylsulfanyl-pyridin-3-ylmethoxy)-5,7-difluoro-2,3-dihydro-benzofuran-3-yl]-acetic acidYield 72%

Procedure

3-Chloromethyl-2-cyclopentylsulfanyl-pyridine (19 mg, 0.08 mmol) obtained in Step C of Preparation Example 8 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 (0.25 mg, 72%).

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-a840b8a943404fe7997a1d2064b6ed52
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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