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

HRID 62947Notes

Reaction equation

HRID 62947 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH:10]([CH3:12])[CH3:11])[N:4]=1.C[O:14][C:15](=[O:27])[CH2:16][CH:17]1[C:21]2[CH:22]=[CH:23][C:24]([OH:26])=[CH:25][C:20]=2[O:19][CH2:18]1>>[CH:10]([S:9][C:5]1[N:4]=[C:3]([CH2:2][O:26][C:24]2[CH:23]=[CH:22][C:21]3[CH:17]([CH2:16][C:15]([OH:27])=[O:14])[CH2:18][O:19][C:20]=3[CH:25]=2)[CH:8]=[CH:7][CH:6]=1)([CH3:12])[CH3:11]

Participants

3

Reactant 2

HCID 57345855Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetateHCID 901181412-Chloromethyl-6-isopropylsulfanyl-pyridine

Product 1

HCID 74222621[6-(6-Isopropylsulfanyl-pyridin-2-ylmethoxy)-2,3-dihydro-benzofuran-3-yl]-acetic acidYield 84%

Procedure

2-Chloromethyl-6-isopropylsulfanyl-pyridine (20 mg, 0.10 mmol) obtained in Step C of Preparation Example 16 and (6-hydroxy-2,3-dihydro-benzofuran-3-yl)-acetic acid methyl ester (20 mg, 0.10 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 (30 mg, 84%).

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-542bb6b5b55c4656a9b905147fe80e5d
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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