Sodium Carbonate → HCID 89961587, compound

HRID 1521622Notes

Reaction equation

HRID 1521622 reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[C:12]([CH2:13][CH2:14][C:5]2=[N:4][N:3]=1)=[CH:11][C:10](B1OC(C)(C)C(C)(C)O1)=[CH:9][CH:8]=3.Br[C:25]1[CH:26]=[N:27][CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>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].O1CCOCC1>[CH3:1][C:2]1[N:6]2[C:7]3[C:12]([CH2:13][CH2:14][C:5]2=[N:4][N:3]=1)=[CH:11][C:10]([C:25]1[CH:26]=[N:27][CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)=[CH:9][CH:8]=3

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 111279913-Bromo-5-(trifluoromethyl)pyridineHCID 70977989HCID 70977989, compound

Product 1

HCID 89961587HCID 89961587, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 1-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline (75-2; 0.5 g, 0.00112 mol) and 3-bromo-5-(trifluoromethyl)pyridine (0.381 g, 0.00168 mol) in the mixture of 1,4-dioxan (10 mL) was added aqueous sodium carbonate (2M) (1.68 mL, 0.003376 mol). Reaction mass was purged with argon for 20 min. Then catalyst Pd(dppf)2Cl2 (0.0459 g, 0.003376 mol) was added and allowed to stir at 80° C. for 12 h. The reaction mixture was filtered through CELITE bed and filter bed was thoroughly washed with ethyl acetate. The collected organic parts were concentrated under vacuum to afford the crude compound, which was purified by silica gel column chromatography to obtain title compound. 1H NMR (400 MHz, DMSO-d6) δ 9.25 (s, 1H), 8.97 (s, 1H), 8.51 (s, 1H), 8.02 (s, 1H), 7.91-7.89 (d, J 8.4 Hz, 1H), 7.78-7.76 (d, J=8 Hz, 1H), 3.04 (s, 4H), 2.70 (s, 3H). MS (M+1): 331.1.

Workup

  1. customReaction mass
  2. customwas purged with argon for 20 min
  3. filtrationThe reaction mixture was filtered through CELITE bed
  4. filtrationfilter bed
  5. washwas thoroughly washed with ethyl acetate
  6. concentrationThe collected organic parts were concentrated under vacuum
  7. customto afford the crude compound, which
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-67b157f55e28464896fcd59f09e4556a
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

Loading…