Ethanol → HCID 59580630, compound

HRID 1803423Notes

Reaction equation

HRID 1803423 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.C(O)C.C([O-])([O-])=O.[K+].[K+].[C:20]([O:24][C:25](=[O:34])[N:26]([C:28]1[S:32][C:31](Br)=[N:30][CH:29]=1)[CH3:27])([CH3:23])([CH3:22])[CH3:21]>C1(C)C=CC=CC=1.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>[C:20]([O:24][C:25](=[O:34])[N:26]([C:28]1[S:32][C:31]([C:5]2[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:30][CH:29]=1)[CH3:27])([CH3:23])([CH3:21])[CH3:22]

Participants

8

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 38450342-Chloropyridine-5-boronic acidHCID 68767163HCID 68767163, compound

Product 1

HCID 59580630HCID 59580630, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 6-chloro-3-pyridine boronic acid (158 mg, 1.0 mmol) in toluene (4 mL) was added absolute ethanol (2 mL) followed by a 2.0 M solution of K2CO3 (1.0 mL). To this mixture was added (2-bromo-thiazol-5-yl)-methyl-carbamic acid tert-butyl ester (322 mg, 1.1 mmol) followed by tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol). The reaction mixture was heated to 100° C. for 16 h. The mixture was cooled and diluted with ethyl acetate. The organic layer was washed with saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated. The organic layer was purified by silica gel chromatography (0-100% ethyl acetate/hexanes) to afford an off-white solid (270 mg, 83%): mp 167-170° C.; 1H NMR (300 MHz, CDCl3) δ 8.88 (br s, 1H), 8.16 (dd J=3.0, 8.0 Hz, 1H), 7.40 (d, J=7.0 Hz, 1H), 7.39 (s, 1H), 3.45 (s, 3H), 1.61 (s, 9H); ESIMS m/z 326 (M+1).

Workup

  1. temperatureThe mixture was cooled
  2. washThe organic layer was washed with saturated aqueous NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe organic layer was purified by silica gel chromatography (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-105d6fd9494c4411957f43545246aeb0
Source dataset
uspto-grants-2013_01
Patent number
US08350044B2

Reaction notes

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