Acetonitrile → HCID 59699766, compound

HRID 729824Notes

Reaction equation

HRID 729824 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[S:12][CH:13]=[CH:14][N:15]=3)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28](B(O)O)[CH:27]=1.C(#N)C.C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:2]2[CH:3]=[C:4]3[C:10]([C:11]4[S:12][CH:13]=[CH:14][N:15]=4)=[CH:9][NH:8][C:5]3=[N:6][CH:7]=2)[CH:27]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 27343783-Pyridinylboronic acidHCID 59700144HCID 59700144, compound

Product 1

HCID 59699766HCID 59699766, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-(5-bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine-3-yl)thiazole (75 mg, 0.17 mmol), pyridine-3-ylboronic acid (27 mg, 0.22 mmol) 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichloromethane adduct (6.9 mg, 0.009 mmol), acetonitrile (1 mL) and saturated aqueous NaHCO3 (1 mL) were stirred in a sealed microwave tube at 140° C. for 30 minutes. The mixture was then cooled to room temperature, diluted with ethyl acetate, washed with brine and concentrated to dryness. Silica gel chromatography afforded 2-(5-(pyridine-3-yl)-1H-pyrrolo[2,3-b]pyridine-3-yl)thiazole (36 mg, 76% yield) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 7.47 (m, 1H), 7.56 (d, J=3.5 Hz, 1H), 7.81 (d, J=3.5 Hz, 1H), 8.10 (m, 1H), 8.24 (s, 1H), 8.55 (dd, J=2.0, 5.0 Hz, 1H), 8.61 (d, J=2.5 Hz, 1H), (d, J=2.0 Hz, 1H), 8.89 (m, 1H), 12.37 (s, 1H). MS: m/z 279.0 (M+H+)

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. washwashed with brine
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-eae7e98ff5dc4db6b2eeb42a7f391998
Source dataset
uspto-grants-2009_09
Patent number
US07582637B2

Reaction notes

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