4-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholine → 5-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

HRID 1851774Notes

Reaction equation

HRID 1851774 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9](F)[CH:8]=[CH:7][C:5]=2[N:6]=1.CC1(C)C(C)(C)OB([C:20]2[CH:21]=[CH:22][C:23]([N:26]3CCOC[CH2:27]3)=[N:24][CH:25]=2)O1.[CH3:33][O:34]C1C=CC2N=C(C3C=NC(N)=NC=3)SC=2C=1>CCCCCCC.CCOC(C)=O>[CH3:33][O:34][C:8]1[CH:9]=[CH:10][C:4]2[S:3][C:2]([C:20]3[CH:21]=[CH:22][C:23]([NH:26][CH3:27])=[N:24][CH:25]=3)=[N:6][C:5]=2[CH:7]=1

Participants

5

Reactant 3

HCID 27953634-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholineHCID 114923512-Bromo-6-fluoro-1,3-benzothiazoleHCID 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-6-fluoro-1,3-benzothiazole (100 mg, 0.43 mmol) and 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]morpholine (150 mg, 0.52 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 (126 mg) as an off-white solid. 1H NMR δ 8.79 (d, 1 H) 8.15 (dd, 1 H) 8.05-7.97 (m, 2 H) 7.40-7.34 (m, 1 H) 6.99 (d, 1 H) 3.73-3.69 (m, 4 H) 3.64-3.60 (m, 4 H); MS m/z (M+H) 316.

Sources & evidence

ORD record
ord-b2518fc0de8e41df9bca21b2093fbc0e
Source dataset
uspto-grants-2015_02
Patent number
US08957215B2

Reaction notes

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