3-Hydroxypyridine → HCID 51037724, compound

HRID 1045810Notes

Reaction equation

HRID 1045810 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[C:5]([NH:7][C:8]1[CH:13]=[C:12](Cl)[CH:11]=[CH:10][N:9]=1)=[O:6].[OH:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl.CN(C)CC(O)=O>O1CCOCC1.[Cu]I>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[C:5]([NH:7][C:8]1[CH:13]=[C:12]([O:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:11]=[CH:10][N:9]=1)=[O:6]

Participants

7

Reactant 4

HCID 79713-HydroxypyridineHCID 10796Cesium carbonateHCID 75605N,N-Dimethylglycine hydrochlorideHCID 3011465HCID 3011465, compound

Product 1

HCID 51037724HCID 51037724, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Compound 1 (50 mg, 0.19 mmol, 1.0 eq), 3-hydroxypyridine (26.7 mg, 0.281 mmol, 1.50 eq), CuI (3.7 mg, 0.019 mmol, 0.10 eq), Cs2CO3 (122 mg, 0.374 mmol, 2.00 eq) and N,N-dimethylglycine hydrochloride (7.8 mg, 0.056 mmol, 0.30 eq) were dissolved in 1,4-dioxane (1 mL) in a flame-dried sealed tube and heated overnight at 90° C. The reaction was cooled to rt, plugged through celite and concentrated. Purification by flash chromatography on silica gel afforded 24 mg (40%) of the title compound as a pale yellow oil: 1H NMR (400 MHz, DMSO-d6) δ 11.06 (s, 1H), 8.55-8.53 (m, 2H), 8.31 (d, J=5.7 Hz, 1H), 8.01 (m, 1H), 7.92 (d, J=7.8 Hz, 1H), 7.79 (d, J=2.3 Hz, 1H), 7.73 (ddd, J=8.4, 2.6, 1.2 Hz, 1H), 7.64 (d, J=8.6 Hz, 1H), 7.55 (dd, J=8.4, 4.7 Hz, 1H), 7.51 (t, J=7.9 Hz, 1H) 6.82, (dd, J=5.7, 2.4 Hz, 1H); ES-MS [M+1]+: 326.1.

Workup

  1. customsealed tube
  2. temperatureThe reaction was cooled to rt
  3. concentrationconcentrated
  4. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-8948a46ed8ef4cbfac4f364bd8beefc9
Source dataset
uspto-grants-2013_10
Patent number
US08569308B2

Reaction notes

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