Cesium carbonate → HCID 67974983, compound

HRID 2174468Notes

Reaction equation

HRID 2174468 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([Cl:21])[CH:6]=[CH:7][C:8]=2[O:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=1.[NH2:22][C:23]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=1.[C:32]([O-])([O-])=O.[Cs+].[Cs+]>CC(O)(C)C.CC([O-])=O.CC([O-])=O.[Pd+2].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[Cl:21][C:5]1[CH:6]=[CH:7][C:8]([O:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[C:9]2[C:4]=1[N:3]=[C:2]([NH:22][C:23]1[C:28]([N+:29]([O-:31])=[O:30])=[C:27]([CH3:32])[CH:26]=[CH:25][N:24]=1)[CH:11]=[CH:10]2

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 778873-Nitropyridin-2-ylamineHCID 86698898HCID 86698898, compound

Product 1

HCID 67974983HCID 67974983, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 6386tert-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

A reaction mixture of 4-(2-((2,8-dichloroquinolin-5-yl)oxy)ethyl)morpholine (81.5 mg, 0.25 mmol, 1 eq.), 2-amino-3-nitropyridine (41.3 mg, 0.27 mmol, 1.1 eq.), Pd(OAc)2 (1.1 mg, 2 mol %), XantPhos (2.9 mg, 2 mol %) and Cs2CO3 (228 mg, 2.8 eq.)) in t-BuOH (1 mL) was heated at 90° C. and stirred for 20 hours. The reaction mixture was then concentrated under reduced pressure and the resulting residue was diluted with ethyl acetate. The organic phase was washed with water, dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to afford 8-chloro-N-(4-methyl-3-nitropyridin-2-yl)-5-(2-morpholinoethoxy)quinolin-2-amine (41 mg, 37%).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additionthe resulting residue was diluted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-956d828eb3994b5b9f1cb0592873614f
Source dataset
uspto-grants-2015_06
Patent number
US09061999B2

Reaction notes

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