Sodium Carbonate → HCID 68569944, compound

HRID 2175138Notes

Reaction equation

HRID 2175138 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][C:9](Br)=[CH:8]2)(=O)C.[CH3:16][N:17]1[CH:21]=[C:20](B2OC(C)(C)C(C)(C)O2)[CH:19]=[N:18]1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.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>[CH3:16][N:17]1[CH:21]=[C:20]([C:9]2[CH:10]=[N:11][C:12]3[C:7]([CH:8]=2)=[CH:6][C:5]([OH:4])=[CH:14][CH:13]=3)[CH:19]=[N:18]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 685300473-Bromoquinolin-6-yl acetate

Product 1

HCID 68569944HCID 68569944, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of Intermediate A (1.8 g, 6.76 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.548 g, 7.44 mmol), Na2CO3 (2.151 g, 20.29 mmol) and Pd(PPh3)4 (0.782 g, 0.676 mmol) in DMF (10 ml) was bubbled with argon for 10 min. Then the mixture was heated at 90° C. for 5 h. After being cooled to rt, the mixture was diluted with EtOAc (40 ml), washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was recrystallized from EtOAc to afford the title compound as pale gray solid (1.1 g, 65% yield). 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.97 (s, 1H), 8.91 (s, 1H), 8.33 (s, 1H), 8.23 (d, 2H), 8.00 (s, 1H), 7.80 (d, 1H), 7.22 (dd, 1H), 7.00 (d, 1H), 3.90 (s, 3H). LCMS (method B): [M+H]+=226, tR=1.41 min.

Workup

  1. customwas bubbled with argon for 10 min
  2. temperatureAfter being cooled to rt
  3. additionthe mixture was diluted with EtOAc (40 ml)
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was recrystallized from EtOAc

Sources & evidence

ORD record
ord-3ca0ab580f18419d9cca5d8d90d112d4
Source dataset
uspto-grants-2015_06
Patent number
US09062045B2

Reaction notes

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