(3-hydroxyphenyl)boronic Acid → 3-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)phenol

HRID 1261260Notes

Reaction equation

HRID 1261260 reaction equation
[F:1][C:2]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12](C3C=CC(O)=CC=3)[S:13][C:6]=12.[OH:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1>>[F:1][C:2]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:33]3[CH:34]=[C:29]([OH:28])[CH:30]=[CH:31][CH:32]=3)[S:13][C:6]=12

Participants

3

Reactant 2

HCID 2734359(3-hydroxyphenyl)boronic AcidHCID 1360596484-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)phenol

Product 1

HCID 594244533-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)phenolYield 66%

Procedure

Starting from the nitrobromo compound 42, following the procedure described above for the synthesis of compound 153 (scheme 28, example 109) but substituting 4-hydroxyphenylboronic acid for 3-hydroxyphenylboronic acid, title compound 160 was obtained in 66% yield as a gray solid. LRMS (M+1) 383.1 (100%).

Sources & evidence

ORD record
ord-22be65248d76419d8a1efcee783b819b
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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