4-Nitrophenol → 7-(4-Nitrophenoxy)thieno[3,2-b]pyridine

HRID 1710992Notes

Reaction equation

ClC1C=CN=C2C=CSC=12.F[C:12]1[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:13]=1[O:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]2[CH:21]=[C:22](C(N(C)C)=O)[S:23][C:16]=12.[N+](C1C=CC(O)=CC=1)([O-])=O>>[N+:33]([C:31]1[CH:30]=[CH:29][C:13]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]3[CH:21]=[CH:22][S:23][C:16]=23)=[CH:12][CH:32]=1)([O-:35])=[O:34]

Participants

Reactant 3

HCID 9804-Nitrophenol

HCID 112752517-Chlorothieno[3,2-b]pyridine

HCID 594244757-(2-fluoro-4-nitrophenoxy)-N,N-dimethylthieno[3,2-b]pyridine-2-carboxamide

Product 1

HCID 594246367-(4-Nitrophenoxy)thieno[3,2-b]pyridineYield 89%

Procedure

Staring from the chloride 2, following the procedure described above for the synthesis of compound 6 (scheme 1, example 1) but substituting 2-fluoro-4-nitrophenol for 4-nitrophenol, title compound 212 was obtained in 89% yield. MS (m/z) 273.0 (M+H).

Sources & evidence

ORD record: ord-b82f24c18aa7456d8821aff37f543057
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790729B2

Reaction notes

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