Trifluoroiodomethane → 3-(benzyloxy)-5-iodo-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride

HRID 1426095Notes

Reaction equation

HRID 1426095 reaction equation
[ClH:1].[CH2:2]([O:9][C:10]1[C:11]([NH:17][C:18]2[S:19][CH:20]=[C:21]([CH3:23])[N:22]=2)=[N:12][CH:13]=[C:14](Br)[CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Li]C.C([Li])CCC.FC([I:35])(F)F>>[ClH:1].[CH2:2]([O:9][C:10]1[C:11]([NH:17][C:18]2[S:19][CH:20]=[C:21]([CH3:23])[N:22]=2)=[N:12][CH:13]=[C:14]([I:35])[CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 16843TrifluoroiodomethaneHCID 160614653-(benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochlorideHCID 178418339ButyllithiumHCID 178418348HCID 178418348, compound

Product 1

HCID 866396523-(benzyloxy)-5-iodo-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochlorideYield 37%

Procedure

3-(Benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine (prepared according to Example 1) (0.250 g, 0.664 mmol), MeLi (0.519 mL, 0.831 mmol), butyllithium (0.332 mL, 0.831 mmol) and trifluoromethyliodide (bubbled in excess) were reacted according to the method of Example 7 to provide 3-(benzyloxy)-5-iodo-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride (0.104 g, 37.0% yield). 1H NMR (d6-DMSO) δ 8.14 (d, 1H), 7.82 (m, 1H), 7.58 (m, 2H), 7.40 (m, 3H), 6.79 (s, 1H), 5.31 (s, 2H), 2.28 (s, 3H). Mass spectrum (apci) m/z=424.0 (M+H).

Sources & evidence

ORD record
ord-7f1d33e78d4c4ef3bf1c22ad83117b99
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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