(6-Methoxypyridin-3-yl)boronic acid → HCID 68739156, compound

HRID 869929Notes

Reaction equation

HRID 869929 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[CH2:19][CH2:18][CH2:17]4)[CH2:13][CH2:12]2)=[O:10])[CH:5]=[CH:4][C:3]=1[CH3:23].[CH3:24][O:25][C:26]1[N:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1>COCCOC.C([O-])([O-])=O.[Na+].[Na+].C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:19]1[C:20]2[C:16](=[CH:15][C:14]([C:11]3([C:9]([NH:8][C:6]4[N:7]=[C:2]([C:29]5[CH:30]=[N:31][C:26]([O:25][CH3:24])=[CH:27][CH:28]=5)[C:3]([CH3:23])=[CH:4][CH:5]=4)=[O:10])[CH2:13][CH2:12]3)=[CH:22][CH:21]=2)[CH2:17][CH2:18]1

Participants

7

Reactant 2

HCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 87556410HCID 87556410, compound

Product 1

HCID 68739156HCID 68739156, compoundYield 93.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
80 °C

Procedure

To N-(6-chloro-5-methylpyridin-2-yl)-1-(2,3-dihydro-1H-inden-5-yl)cyclopropanecarboxamide (0.132 g, 0.4030 mmol), 6-methoxypyridin-3-ylboronic acid (0.092 g, 0.6045 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.046 g, 0.04030 mmol) in 1,2-dimethoxyethane (4.4 mL), 2 M Na2CO3 (600 μL) was added. The reaction mixture was stirred and heated at 80° C. for 22 hours under N2 atmosphere. The reaction mixture was diluted with ethyl acetate (5 mL), dried over Na2SO4, filtered and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel (0-30% ethyl acetate in hexane) to yield 1-(2,3-dihydro-1H-inden-5-yl)-N-(6′-methoxy-3-methyl-2,3′-bipyridin-6-yl)cyclopropanecarboxamide as a white solid (0.150 g, 93.17%). ESI-MS m/z calc. 399.48, found 400.5 (M+1)+. Retention time 2.17 minutes.

Workup

  1. dry with materialdried over Na2SO4
  2. filtrationfiltered
  3. customevaporated under reduced pressure
  4. customThe crude product was purified by column chromatography on silica gel (0-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9fd520d413294ca284973f59c849bb36
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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