Sodium Carbonate → HCID 117667152, compound

HRID 712663Notes

Reaction equation

HRID 712663 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14](Br)=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].[CH2:42]([O:49][C:50]1[CH:51]=[N:52][CH:53]=[C:54](Br)[CH:55]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:54]3[CH:53]=[N:52][CH:51]=[C:50]([O:49][CH2:42][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH:55]=3)=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 11833959tert-Butyl 6-bromo-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylateHCID 153891983-(Benzyloxy)-5-bromopyridine

Product 1

HCID 117667152HCID 117667152, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6-bromo-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (800 mg, 2.6 mmol) in 1,4-dioxane (64 mL) is added bis(pinacolato)diboron (714 mg, 2.8 mmol), 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium (II) (187 mg, 0.26 mmol) and potassium acetate (751 mg, 7.7 mmol) under nitrogen. The resultant mixture is heated to reflux for 2 h. After cooling to rt, 3-benzyloxy-5-bromo-pyridine (677 mg, 2.6 mmol), sodium carbonate (815 mg, 7.7 mmol) and additional 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium (II) (94 mg, 0.13 mmol) are added under nitrogen. The reaction is heated to reflux for 16 h. The crude product is purified by silica gel column to obtain 6-(5-benzyloxy-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (790 mg).

Workup

  1. temperatureto reflux for 2 h
  2. temperatureThe reaction is heated
  3. temperatureto reflux for 16 h
  4. customThe crude product is purified by silica gel column

Sources & evidence

ORD record
ord-6cb7d886f5104f85be8f831f239ec1b4
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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