(2-Methoxypyridin-3-yl)boronic acid → HCID 59165899, compound

HRID 869959Notes

Reaction equation

HRID 869959 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:21]=[CH:20][CH:19]=[C:18](Br)[N:17]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:23][O:24][C:25]1[C:30](B(O)O)=[CH:29][CH:28]=[CH:27][N:26]=1>C(O)C.C(=O)([O-])[O-].[K+].[K+]>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[N:17]=[C:18]([C:30]5[C:25]([O:24][CH3:23])=[N:26][CH:27]=[CH:28][CH:29]=5)[CH:19]=[CH:20][CH:21]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 2

HCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 591658951-(Benzo[d][1,3]dioxol-6-yl)-N-(6-bromopyridin-2-yl)cyclopropanecarboxamide

Product 1

HCID 59165899HCID 59165899, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
110 °C

Procedure

1-(Benzo[d][1,3]dioxol-5-yl)-N-(6-bromopyridin-2-yl)cyclopropanecarboxamide (36 mg, 0.10 mmol) was dissolved in 1 mL of ethanol containing 0.12 mL of a 2 M aqueous solution of potassium carbonate, 2-methoxypyridin-3-ylboronic acid (18 mg, 0.12 mmol) and 6 mg of Fibre-Cat 1007. The reaction mixture was then heated to 110° C. for 10 minutes in a microwave reactor. The resulting material was cooled to room temperature, filtered, and purified by reverse-phase preparative liquid chromatography utilizing a gradient of 0-99% acetonitrile in water containing 0.05% trifluoroacetic acid to yield the pure product. ESI-MS m/z calc. 389.1. found 390.1 (M+1)+. Retention time 3.09 minutes.

Workup

  1. temperatureThe resulting material was cooled to room temperature
  2. filtrationfiltered
  3. custompurified by reverse-phase preparative liquid chromatography
  4. customto yield the pure product

Sources & evidence

ORD record
ord-27f9cfa36b1e4e4e94e350e3f12dadd8
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

Loading…