2-(5-(1,3-Dioxan-2-yl)-1-methyl-1H-imidazol-2-yl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine → 2-(5-(1,3-Dioxolan-2-yl)pyridin-2-yl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

HRID 84381Notes

Reaction equation

HRID 84381 reaction equation
O1CCCOC1C1N(C)C(C2SC3C(=NC=CC=3[O:22][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][C:24]=3[F:32])C=2)=NC=1.[O:33]1[CH2:37][CH2:36][O:35][CH:34]1[C:38]1[CH:39]=[CH:40][C:41]([C:44]2[S:52][C:51]3[C:46](=[N:47][CH:48]=[CH:49][C:50]=3Cl)[CH:45]=2)=[N:42][CH:43]=1>>[O:33]1[CH2:37][CH2:36][O:35][CH:34]1[C:38]1[CH:39]=[CH:40][C:41]([C:44]2[S:52][C:51]3[C:46](=[N:47][CH:48]=[CH:49][C:50]=3[O:22][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][C:24]=3[F:32])[CH:45]=2)=[N:42][CH:43]=1

Participants

3

Reactant 2

HCID 579195272-(5-(1,3-Dioxan-2-yl)-1-methyl-1H-imidazol-2-yl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridineHCID 579195542-(5-(1,3-Dioxolan-2-yl)pyridin-2-yl)-7-chlorothieno[3,2-b]pyridine

Product 1

HCID 579194962-(5-(1,3-Dioxolan-2-yl)pyridin-2-yl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridineYield 72%

Procedure

Following the procedure described above for the synthesis of compound 41 (scheme 1) but substituting compound 40 for compound 137, title compound 138 was obtained in 72% yield. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.68 (d, J=1.8 Hz, 1H), 8.64 (d, J=5.5 Hz, 1H), 8.49 (dd, J=10.4, 2.5 Hz, 1H), 8.47 (s, 1H), 8.35 (d, J=8.4 Hz, 1H), 8.23-8.21 (m, 1H), 8.00 (dd, J=8.2, 2.0 Hz, 1H), 7.73 (t, J=8.5 Hz, 1H), 6.99 (d, J=5.5 Hz, 1H), 5.89 (s, 1H), 4.12-4.06 (m, 2H), 4.04-3.98 (m, 2H). MS (m/z): 440.1 (M+H).

Sources & evidence

ORD record
ord-85fb39dd9ccc4d2aa91acf8cdd024d62
Source dataset
uspto-grants-2014_09
Patent number
US08846927B2

Reaction notes

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