Diisopropyl malonate → 4-(3-Fluoro-benzyl)-7-hydroxy-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid

HRID 902493Notes

Reaction equation

HRID 902493 reaction equation
C([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[C:9]2[CH:21]=[CH:22][S:23][C:8]=2[C:7]=1[OH:24])=[O:5])C.C(OC(C)C)(=O)CC(OC(C)C)=O>>[F:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][N:10]1[C:11](=[O:12])[C:6]([C:4]([OH:5])=[O:3])=[C:7]([OH:24])[C:8]2[S:23][CH:22]=[CH:21][C:9]1=2

Participants

3

Reactant 2

HCID 83223Diisopropyl malonateHCID 693160674-(3-Fluoro-benzyl)-7-hydroxy-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 693161704-(3-Fluoro-benzyl)-7-hydroxy-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid

Procedure

This compound was prepared by using the same procedure as described for 4-(3-fluoro-benzyl)-7-hydroxy-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (15) by using diisopropyl malonate. 1H-NMR (DMSO-d6) δ 1.30 (d, J=6.4 Hz, 6H), 5.17 (m, 1H), 5.36 (s, 2H), 7.08 (m, 3H), 7.31 (m, 2H), 8.15 (dd, J=2.4, 5.2 Hz, 1H), 13.41 (b, 1H) ppm; EIMS m/z 362 (M+1).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-6eaed10e8cf649129acd9bd5e34d00d2
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

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