Ammonia → 2-[3-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]acetamide

HRID 1050051Notes

Reaction equation

HRID 1050051 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:17][C:18]([O:20]C)=O)[CH:5]=[CH:6][C:7]=1[B:8]1[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]1.[NH3:22]>>[F:1][C:2]1[CH:3]=[C:4]([CH2:17][C:18]([NH2:22])=[O:20])[CH:5]=[CH:6][C:7]=1[B:8]1[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 59627674Methyl 2-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate

Product 1

HCID 904161632-[3-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]acetamideYield 84.1%

Procedure

A solution of methyl 2-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate (0.1 g, 0.340 mmol) in ammonia (MeOH, 10 mL, 160 mmol) was stirred at 20° C. for 16 h. After LCMS analysis showed the starting material had disappeared, the solvent was removed in vacuo to yield 2-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide (100 mg, 0.286 mmol, 84.0% yield): 1H NMR (400 MHz, DMSO-d6) δ 7.56 (t, J=7.2 Hz, 1H), 7.14-6.98 (m, 2H), 3.59 (s, 2H), 1.26 (s, 12H); ES-LCMS m/z 280.1 (M+H).

Workup

  1. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cb02544f48ef486d9b97c0949fa63297
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

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