2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 4-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholine

HRID 2224305Notes

Reaction equation

HRID 2224305 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(O[B:18]1[O:22][C:21]([CH3:24])([CH3:23])[C:20]([CH3:26])([CH3:25])[O:19]1)(C)C.COC1C=CC(B2OC(C)(C)C(C)(C)O2)=CN=1>>[CH3:25][C:20]1([CH3:26])[C:21]([CH3:24])([CH3:23])[O:22][B:18]([C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[N:6][CH:7]=2)[O:19]1

Participants

4

Reactant 3

HCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 109667244-(5-bromopyridin-2-yl)morpholineHCID 162177142-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Product 1

HCID 27953634-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholineYield 71%

Procedure

Compound 5A (616 mg, 71%) was prepared from 4-(5-bromo-pyridin-2-yl)-morpholine (727 mg, 2.99 mmol) and 2-isopropoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (0.915 mL, 4.49 mmol) by a route analogous to that used for the preparation of 2A.

Sources & evidence

ORD record
ord-44a4e581a105453d9418872401eb80f9
Source dataset
uspto-grants-2008_05
Patent number
US07378426B2

Reaction notes

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