Ethyl 4-hydroxy-1H-indole-2-carboxylate → 4-(Tetrahydro-furan-3-ylmethoxy)-1H-indole-2-carboxylic acid

Reaction equation

[CH:1]1([CH2:5][O:6][C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH:9]=[C:10]([C:16]([OH:18])=[O:17])[NH:11]3)[CH2:4][CH2:3][CH2:2]1.C([O:21]C(C1NC2C(C=1)=C(O)C=CC=2)=O)C>>[O:21]1[CH2:3][CH2:4][CH:1]([CH2:5][O:6][C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH:9]=[C:10]([C:16]([OH:18])=[O:17])[NH:11]3)[CH2:2]1

Participants

Reactant 2

HCID 13274763Ethyl 4-hydroxy-1H-indole-2-carboxylate

HCID 591526824-Cyclobutylmethoxy-1H-indole-2-carboxylic acid

Product 1

HCID 591526504-(Tetrahydro-furan-3-ylmethoxy)-1H-indole-2-carboxylic acid

Procedure

4-(Tetrahydro-furan-3-ylmethoxy)-1H-indole-2-carboxylic acid (16b) is synthesized analogous to 16a from 4-(tetrahydro-furan-3-yl)methanol and 4-hydroxy-1H-indole-2-carboxylic acid ethyl ester.

Sources & evidence

ORD record: ord-8cd33c39341e4740aa57a958e6d283fb
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354431B2

Reaction notes

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