Cesium fluoride → 5,7-Diphenyl-8-aminoquinoline

HRID 1014781Notes

Reaction equation

HRID 1014781 reaction equation
Br[C:2]1[CH:11]=[C:10](Br)[C:9]([NH2:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[F-].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)C2[C-](N(C)C)C=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[C:14]1([C:2]2[CH:11]=[C:10]([C:2]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:3]=3)[C:9]([NH2:13])=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[N:7]3)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 66827Phenylboronic AcidHCID 6273845,7-Dibromoquinolin-8-amine

Product 1

HCID 673164155,7-Diphenyl-8-aminoquinolineYield 175.9%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1317290462-Diphenylphosphino-dimethylaminoferroceneCatalystHCID 312751,4-DioxaneSolvent

Procedure

According to General Procedure A, a mixture of 5,7-dibromo-8-aminoquinoline (14 g, 100 mg, 0.33 mmol), phenylboronic acid (60 mg, 0.50 mmol), CsF (150 mg, 0.99 mmol), Pd(OAc)2 (1.3 mg, 0.007 mmol) and ligand 12f (5.3 mg, 0.013 mmol) in 1,4-dioxane (2.5 mL) was heated to reflux, cooled and filtered. After evaporation of the solvent, recrystallization from Et2O/hexane gave 51g (86 mg, 88%) as colorless crystals. mp: 100-102° C. (Et2O/hexane). IR (KBr): vmax 3450, 3347, 3050, 3023, 1583 cm−1. 1H NMR (300 MHz, CDCl3): δ 8.85-8.80 (m, 1H), 8.28 (dd, 1H, J=8.4, 1.5 Hz), 7.66-7.63 (m, 2H), 7.54-7.44 (m, 6H), 7.42-7.34 (m, 4H), 5.32 (s, 2H). 13C NMR (75.5 MHz, CDCl3): δ 147.5, 140.2, 139.9, 138.3, 134.2, 130.2, 130.0, 129.2, 129.0, 128.4, 128.2, 127.2, 126.8, 126.1, 121.7, 121.2. EIMS (m/z, (%)): 296 (72), 219 (24), 86 (100), 47 (85). HRMS (EI; m/z): calcd for C21H16N2: 296.1314. Found 296.1312.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperaturecooled
  4. filtrationfiltered
  5. customAfter evaporation of the solvent, recrystallization from Et2O/hexane

Sources & evidence

ORD record
ord-da28693ade1c441dae729d9ebc2a24cb
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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