Sodium Carbonate → HCID 86696255, compound

HRID 2175133Notes

Reaction equation

HRID 2175133 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:8])=[N:6][CH:7]=1.[O:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[O:15][CH2:16][CH2:17][N:18]1[CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:20]=[N:19]1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:8][C:5]1[CH:4]=[CH:3][C:2]([C:21]2[CH:20]=[N:19][N:18]([CH2:17][CH2:16][O:15][CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][O:9]3)[CH:22]=2)=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27831685-Bromo-2-fluoropyridineHCID 593418191-[2-(oxan-2-yloxy)ethyl]-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 86696255HCID 86696255, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 5-bromo-2-fluoropyridine (176 mg, 1.00 mmol), 1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (322 mg, 1.00 mmol), Pd(PPh3)4 (115 mg, 0.100 mmol) and Na2CO3 (212 mg, 2.00 mmol) in 1,4-dioxane (5 ml) was bubbled with N2 for 10 min and then stirred at 85° C. for 6 h. After being cooled to rt, the reaction mixture was filtered through celite and the filtrate was diluted with EA. The organic phase was washed with water, brine and dried over anhydrous MgSO4. Filtered and concentrated to afford the title compound (0.206 g, yield 63.6%), which was used in next step without further purification. 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.48 (s, 1H), 8.27 (s, 1H), 8.17 (dd, 1H), 7.98 (s, 1H), 7.19 (d, 1H), 4.53 (s, 1H), 4.30 (t, 2H), 3.95 (m, 1H), 3.75 (m, 1H), 3.53 (m, 1H), 3.35 (t, 1H), 1.65 (m, 1H), 1.57 (m, 1H), 1.40 (m, 4H). LCMS (method B): [M+H]+=292, tR=2.16 min.

Workup

  1. customwas bubbled with N2 for 10 min
  2. temperatureAfter being cooled to rt
  3. filtrationthe reaction mixture was filtered through celite
  4. additionthe filtrate was diluted with EA
  5. washThe organic phase was washed with water, brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationFiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a61d69bd54ff439fb4e7a7cca52189c4
Source dataset
uspto-grants-2015_06
Patent number
US09062045B2

Reaction notes

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