1,10-Phenanthroline → tert-Butyl 1-(1-(7-methoxyquinolin-4-yloxy)-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridin-3-ylcarbamate

HRID 1878722Notes

Reaction equation

HRID 1878722 reaction equation
[OH:1][CH2:2][C:3]([N:6]1[C:11](=[O:12])[CH:10]=[CH:9][C:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:7]1)([CH3:5])[CH3:4].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[C:42]1[C:51]2[C:46](=[CH:47][C:48]([O:52][CH3:53])=[CH:49][CH:50]=2)[N:45]=[CH:44][CH:43]=1>CN(C=O)C.[Cu]I>[CH3:53][O:52][C:48]1[CH:47]=[C:46]2[C:51]([C:42]([O:1][CH2:2][C:3]([N:6]3[C:11](=[O:12])[CH:10]=[CH:9][C:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:7]3)([CH3:5])[CH3:4])=[CH:43][CH:44]=[N:45]2)=[CH:50][CH:49]=1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 177506514-Iodo-7-methoxyquinolineHCID 69231018tert-Butyl 1-(1-hydroxy-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridin-3-ylcarbamate

Product 1

HCID 59843045tert-Butyl 1-(1-(7-methoxyquinolin-4-yloxy)-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridin-3-ylcarbamate

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of tert-butyl 1-(1-hydroxy-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridin-3-ylcarbamate (275 mg, 974 μmol), 1,10-phenanthroline (35 mg, 195 μmol), cesium carbonate (635 mg, 1948 μmol), copper(I) iodide (19 mg, 97 μmol), and 4-iodo-7-methoxyquinoline in DMF (4 mL) was heated to 100° C. for 2 h. The reaction mixture was partitioned between CH2Cl2 (50 mL) and 5% NaHCO3 (25 mL). The aqueous was extracted twice with CH2Cl2 (5 mL). The combined extracts were concentrated onto dry silica (10 g) and purified on 80 grams of silica eluting with 0-6% 2M NH3 in MeOH/CH2Cl2. MS (ESI pos. ion) m/z (MH+): 440. Calc'd exact mass for C24H29N3O5: 439.

Workup

  1. customThe reaction mixture was partitioned between CH2Cl2 (50 mL) and 5% NaHCO3 (25 mL)
  2. extractionThe aqueous was extracted twice with CH2Cl2 (5 mL)
  3. concentrationThe combined extracts were concentrated onto dry silica (10 g)
  4. custompurified on 80 grams of silica eluting with 0-6% 2M NH3 in MeOH/CH2Cl2

Sources & evidence

ORD record
ord-f10c821af45d41aa825a3b34dc1c68b3
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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