Thiophene-3-boronic acid → 4-Hydroxy-6-oxo-3-(4-thien-3-ylphenyl)-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

HRID 1244106Notes

Reaction equation

HRID 1244106 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([OH:17])=[C:14]([C:18]#[N:19])[C:13](=[O:20])[NH:12][C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1.[S:21]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22]1.OC1C=CC(B(O)O)=CC=1>>[OH:17][C:15]1[C:16]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:23]4[CH:24]=[CH:25][S:21][CH:22]=4)=[CH:3][CH:4]=3)=[CH:9][S:10][C:11]=2[NH:12][C:13](=[O:20])[C:14]=1[C:18]#[N:19]

Participants

4

Reactant 3

HCID 581760Thiophene-3-boronic acidHCID 27343604-Hydroxyphenylboronic acidHCID 546964233-(4-Bromophenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

Product 1

HCID 547184954-Hydroxy-6-oxo-3-(4-thien-3-ylphenyl)-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

Procedure

Example 109 was prepared from 3-(4-Bromo-phenyl)-4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile (Example 9) using the same procedure as described for Example 189 substituting 3-thiopheneboronic acid for 4-hydroxyphenyl boronic acid. MS (ESI) m/z 350.9 (M+H+); 1H NMR (300 MHz, DMSO-d6) δ ppm 7.91 (dd, 1H), 7.71 (d, 2H), 7.65 (dd, 1H), 7.60 (dd, 1H), 7.45 (d, 1H).

Sources & evidence

ORD record
ord-8c830c81b3ca4cc8af0e3973a8b8a5be
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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