Morpholine → 1-Morpholino-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone

HRID 1959971Notes

Reaction equation

HRID 1959971 reaction equation
[CH3:1][C:2]1([CH3:19])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=2)[O:3]1.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>>[CH3:1][C:2]1([CH3:19])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[CH:11][C:12]([CH2:15][C:16]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:18])=[CH:13][CH:14]=2)[O:3]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 37190022-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic Acid

Product 1

HCID 593926601-Morpholino-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanoneYield 35%

Procedure

Using 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylacetic acid (786 mg, 3.0 mmol) and morpholine (1.3 mL, 15.0 mmol), the desired title compound (346 mg, yield 35%) was obtained by the same method as the amidation step in Example 4 (4b).

Sources & evidence

ORD record
ord-4b0240a9e6b94a8f9564ab0747d4f7a3
Source dataset
uspto-grants-2013_04
Patent number
US08410273B2

Reaction notes

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