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

HRID 1851773Notes

Reaction equation

HRID 1851773 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.CC1(C)C(C)(C)OB([C:19]2[CH:20]=[CH:21][C:22]([N:25]3CCOC[CH2:26]3)=[N:23][CH:24]=2)O1.[CH3:32][O:33]C1C=CC2N=C(C3C=NC(N)=NC=3)SC=2C=1>CCCCCCC.CCOC(C)=O>[CH3:32][O:33][C:8]1[CH:9]=[CH:10][C:4]2[S:3][C:2]([C:19]3[CH:20]=[CH:21][C:22]([NH:25][CH3:26])=[N:23][CH:24]=3)=[N:6][C:5]=2[CH:7]=1

Participants

5

Reactant 3

HCID 6120402-Bromo-1,3-benzothiazoleHCID 27953634-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholineHCID 248040695-(6-Methoxy-1,3-benzothiazol-2-yl)pyrimidin-2-amine

Product 1

HCID 248037275-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

2-Bromo-1,3-benzothiazole (100 mg, 0.47 mmol) and 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]morpholine (163 mg, 0.56 mmol) were reacted according to the procedure used for the preparation of 5-(6-methoxy-1,3-benzothiazol-2-yl)pyrimidin-2-amine. Flash chromatography (Heptane/EtOAc 1:1) furnished the title compound (73 mg) as an off-white solid. 1H NMR δ 8.81 (d, 1 H) 8.18 (dd, 1 H) 8.10 (d, 1H) 7.98 (d, 1 H) 7.54-7.48 (m, 1 H) 7.44-7.38 (m, 1 H) 7.00 (d, 1 H) 3.74-3.70 (m, 4 H) 3.65-3.60 (m, 4 H); MS m/z (M+H) 298.

Sources & evidence

ORD record
ord-f8d24823b0674c4da786ce518474df6a
Source dataset
uspto-grants-2015_02
Patent number
US08957215B2

Reaction notes

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