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Cesium carbonate → 6-(benzyloxy)-N-(4-tert-butylbenzyl)-2-methyl-1,8-naphthyridine-3-carboxamide

HRID 1961477
Notes
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Reaction equation

HRID 1961477 reaction equation
[C:1]([C:5]1[CH:26]=[CH:25][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:14]([CH3:24])=[N:15][C:16]3[C:21]([CH:22]=2)=[CH:20][C:19](I)=[CH:18][N:17]=3)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:27]([O-:30])([O-])=O.[Cs+].[Cs+].CC1C=N[C:37]2[C:46](C=1C)=[CH:45][CH:44]=[C:43]1[C:38]=2N=CC(C)=C1C>C(O)C1C=CC=CC=1.[Cu]I>[CH2:27]([O:30][C:19]1[CH:20]=[C:21]2[C:16](=[N:17][CH:18]=1)[N:15]=[C:14]([CH3:24])[C:13]([C:11]([NH:10][CH2:9][C:8]1[CH:25]=[CH:26][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=1)=[O:12])=[CH:22]2)[C:37]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:38]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineHCID 66746137N-(4-tert-butylbenzyl)-6-iodo-2-methyl-1,8-naphthyridine-3-carboxamide

Product 1

HCID 667454906-(benzyloxy)-N-(4-tert-butylbenzyl)-2-methyl-1,8-naphthyridine-3-carboxamideYield 235.1%

Reagents, catalysts & solvents 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 244Benzyl AlcoholSolvent

Conditions

Temperature
120 °C

Procedure

In a screw cap pressure tube were N-(4-tert-butylbenzyl)-6-iodo-2-methyl-1,8-naphthyridine-3-carboxamide (135 mg, 0.30 mmol), Cs2CO3 (191.5 mg, 0.6 mmol), CuI (5.6 mg, 0.03 mmol) and 3,4,7,8-tetramethyl-1,10-phenantroline (14.0 mg, 0.06 mmol)) suspended in benzyl alcohol (4.5 ml). N2 was bubbled through the suspension for 5 min. The tube was sealed and the mixture heated to 120° C. overnight. The mixture was allowed to cool. CH2Cl2 was added and the mixture washed with H2O, dried (MgSO4), filtered and concentrated. The crude mixture was purified by flash chromatography (CH2Cl2/MeOH 98:2→97:3) yielding 62 mg of the title compound (47%).

Workup

  1. customIn a screw cap pressure tube
  2. customN2 was bubbled through the suspension for 5 min
  3. customThe tube was sealed
  4. temperatureto cool
  5. additionCH2Cl2 was added
  6. washthe mixture washed with H2O
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude mixture was purified by flash chromatography (CH2Cl2/MeOH 98:2→97:3)

Sources & evidence

ORD record
ord-6d277d7471d1496ab58ea35c98806e13
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08415333B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes