2-Bromo-5-(1,3-dioxolan-2-YL)pyridine → 2-(5-(1,3-Dioxolan-2-yl)pyridin-2-yl)-7-chlorothieno[3,2-b]pyridine

HRID 1047428Notes

Reaction equation

HRID 1047428 reaction equation
[O:1]1[CH2:6]C[CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3[Cl:22])[CH:14]=2)=[N:11][CH:12]=1.BrC1C=CC(C2OCCO2)=CN=1>>[O:1]1[CH2:6][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3[Cl:22])[CH:14]=2)=[N:11][CH:12]=1

Participants

3

Reactant 2

HCID 184696682-Bromo-5-(1,3-dioxolan-2-YL)pyridineHCID 579672702-(5-(1,3-Dioxan-2-yl)pyridin-2-yl)-7-chlorothieno[3,2-b]pyridine

Product 1

HCID 579195542-(5-(1,3-Dioxolan-2-yl)pyridin-2-yl)-7-chlorothieno[3,2-b]pyridineYield 79%

Procedure

Following the procedure described above for the synthesis of compound 29 (Scheme 8) but substituting compound 28 for compound 35, title compound 36 was obtained in 79% yield. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.70 (d, J=1.8 Hz, 1H), 8.67 (d, J=5.1 Hz, 1H), 8.48 (s, 1H), 8.35 (d, J=8.4 Hz, 1H), 8.00 (dd, J=8.2, 2.1 Hz, 1H), 7.61 (d, J=5.1 Hz, 1H), 5.90 (s, 1H), 4.13-4.07 (m, 2H), 4.05-3.99 (m, 2H). MS (m/z): 319.2 (M+H).

Sources & evidence

ORD record
ord-2ebfaf3a34374d8585a859be2f99d130
Source dataset
uspto-grants-2013_10
Patent number
US08569503B2

Reaction notes

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