Potassium Carbonate → HCID 71143769, compound

HRID 1396212Notes

Reaction equation

HRID 1396212 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.C([O-])([O-])=O.[K+].[K+].Br[C:13]1[CH:14]=[CH:15][C:16]([C:19]([F:37])([F:36])[C:20]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=2[F:35])([OH:27])[CH2:21][N:22]2[CH:26]=[N:25][N:24]=[N:23]2)=[N:17][CH:18]=1>[Cu]>[N:1]1[N:2]([C:13]2[CH:14]=[CH:15][C:16]([C:19]([F:36])([F:37])[C:20]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=3[F:35])([OH:27])[CH2:21][N:22]3[CH:26]=[N:25][N:24]=[N:23]3)=[N:17][CH:18]=2)[N:3]=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 71142816HCID 71142816, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 71143769HCID 71143769, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
140 °C

Procedure

To a stirred solution of 1H-1,2,3-triazole (410 mg, 5.93 mmol) were added copper (Cu) powder (93 mg, 1.45 mmol), K2CO3 (160 mg, 1.15 mmol) and 1 (300 mg, 0.694 mmol) under N2 atmosphere. The reaction mixture was gradually heated to 140° C. and stirred for 4 h. The reaction mixture was cooled to 100° C., quenched with ethylenediaminetetraacetic acid (EDTA) sodiuim (Na) salt solution, and made basic with sodium carbonate (Na2CO3) solution. The aqueous layer was extracted with CH2Cl2 (3×50 mL); the combined organic phases were washed with brine, dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude material was purified by silica gel column chromatography (eluting with 45% EtOAc/hexane) to afford 9 (0.12 g, 0.297 mmol, 42%) as a solid. 1H NMR (500 MHz, CDCl3): δ 9.33 (s, 1H), 8.77 (s, 1H), 8.47 (dd, J=8.5, 2.0 Hz, 1H), 7.90 (s, 2H), 7.70 (d, J=9.0 Hz, 1H), 7.34-7.29 (m, 1H), 6.78-6.73 (m, 1H), 6.67-6.64 (m, 1H), 5.64 (d, J=14.0 Hz, 1H), 5.14 (d, J=14.0 Hz, 1H). MS (ESI): m/z 420.9 [M++1]. HPLC: 99.9%.

Workup

  1. temperatureThe reaction mixture was cooled to 100° C.
  2. customquenched with ethylenediaminetetraacetic acid (EDTA) sodiuim (Na) salt solution
  3. extractionThe aqueous layer was extracted with CH2Cl2 (3×50 mL)
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated under reduced pressure
  7. customThe crude material was purified by silica gel column chromatography (eluting with 45% EtOAc/hexane)

Sources & evidence

ORD record
ord-39699ae127dd4d58b4d50aa065111f97
Source dataset
uspto-grants-2014_12
Patent number
US08901121B2

Reaction notes

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