4-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholine → 2-(6-Morpholin-4-ylpyridin-3-yl)-1,3-benzothiazol-6-ol

HRID 1851777Notes

Reaction equation

HRID 1851777 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([OH:11])[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]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[N:24][CH:25]=2)O1.COC1C=CC2N=C(C3C=NC(N)=NC=3)SC=2C=1>>[N:26]1([C:23]2[N:24]=[CH:25][C:20]([C:2]3[S:3][C:4]4[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=4[N:6]=3)=[CH:21][CH:22]=2)[CH2:27][CH2:28][O:29][CH2:30][CH2:31]1

Participants

4

Reactant 3

HCID 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-amineHCID 451167822-Bromo-1,3-benzothiazol-6-ol

Product 1

HCID 248042322-(6-Morpholin-4-ylpyridin-3-yl)-1,3-benzothiazol-6-olYield 39.4%

Procedure

2-Bromo-1,3-benzothiazol-6-ol (40 mg, 0.17 mmol) and 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]morpholine (61 mg, 0.21 mmol) were reacted according to the procedure used for the preparation of 5-(6-methoxy-1,3-benzothiazol-2-yl)pyrimidin-2-amine The reaction mixture was cooled to rt and concentrated. Flash chromatography (Heptane/EtOAc 1:1) gave the title compound (21 mg) as an off-white solid. 1H NMR δ 9.80 (br s, 1 H) 8.71 (d, 1 H) 8.09 (dd, 1 H) 7.77 (d, 1 H) 7.37 (d, 1 H) 6.98-6.93 (m, 2 H) 3.73-3.69 (m, 4 H) 3.61-3.56 (m, 4 H); MS ink (M+H) 314.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-e64b6ee5aefb4d1ba8429eb32da542d9
Source dataset
uspto-grants-2015_02
Patent number
US08957215B2

Reaction notes

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