Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetate → [6-(2-Cyclopentylsulfanyl-pyridin-3-ylmethoxy)-2,3-dihydro-benzofuran-3-yl]-acetic acid

HRID 62953Notes

Reaction equation

HRID 62953 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:29])[CH2:18][CH:19]1[C:23]2[CH:24]=[CH:25][C:26]([OH:28])=[CH:27][C:22]=2[O:21][CH2:20]1>>[CH:10]1([S:9][C:4]2[C:3]([CH2:2][O:28][C:26]3[CH:25]=[CH:24][C:23]4[CH:19]([CH2:18][C:17]([OH:29])=[O:16])[CH2:20][O:21][C:22]=4[CH:27]=3)=[CH:8][CH:7]=[CH:6][N:5]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 57345855Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetateHCID 901182833-Chloromethyl-2-cyclopentylsulfanyl-pyridine

Product 1

HCID 74222708[6-(2-Cyclopentylsulfanyl-pyridin-3-ylmethoxy)-2,3-dihydro-benzofuran-3-yl]-acetic acidYield 70.5%

Procedure

3-Chloromethyl-2-cyclopentylsulfanyl-pyridine (0.21 g, 0.92 mmol) obtained in Step C of Preparation Example 8 and (6-hydroxy-2,3-dihydro-benzofuran-3-yl)-acetic acid methyl ester (0.19 g, 0.92 mmol) obtained in Preparation Example 52 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 g, 70%).

Workup

  1. customobtained in Preparation Example 52
  2. customto react sequentially in the same manner as in Steps A and B of Example 1

Sources & evidence

ORD record
ord-d94f11566f85424785392140e037f81d
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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