Dimethylformamide → 5-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

HRID 1698089Notes

Reaction equation

CO[C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][S:9][C:5]=2[CH:4]=1.Br[C:13]1[N:18]=[CH:17][C:16](N(C)C)=[CH:15][CH:14]=1.[CH3:22][O:23]C1C=CC2N=C(C3C=CC(C(F)(F)F)=CN=3)SC=2C=1.[CH3:43][N:44](C=O)C>[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[CH3:22][O:23][C:11]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:16]3[CH:15]=[CH:14][C:13]([NH:44][CH3:43])=[N:18][CH:17]=3)=[N:7][C:6]=2[CH:10]=1

Participants

Conditions

Temperature: 150 °C

Procedure

6-Methoxy-1,3-benzothiazole (0.136 g, 0.82 mmol; M. A. Matulenko et al. Bioorg. Med. Chem. 2005, 13, 3705.) and 6-bromo-N,N-dimethylpyridin-3-amine (0.199 g, 0.99 mmol) were reacted according to the procedure used for the preparation of 6-methoxy-2-[5-(trifluoromethyl)pyridin-2-yl]-1,3-benzothiazole, with the following exceptions: 10 mol % bis(tri-t-butylphosphine) palladium (0) was used, the amount of DMF was reduced (2 mL) and the reaction mixture was heated at 150° C. for 4.5 h before it was filtered through a short plug of silica that was rinsed by DCM and DMF. The solvents were evaporated under reduced pressure and the residue was subjected to flash chromatography (Heptane/EtOAc gradient). The title compound (0.100 g) was isolated as a yellow solid. 1H NMR (CHLOROFORM-d) δ 8.19-8.15 (m, 2H) 7.90 (d, 1H) 7.38 (d, 1H) 7.09-7.04 (m, 2H) 3.90 (s, 3H) 3.10 (s, 6H); MS m/z (M+H) 286.

Workup

filtrationwas filtered through a short plug of silica that
washwas rinsed by DCM and DMF
customThe solvents were evaporated under reduced pressure

Sources & evidence

ORD record: ord-bc0905e164874b6b90635e8b14d97ef7
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163928B2

Reaction notes

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