Sodium Carbonate → HCID 56599239, compound

HRID 2174956Notes

Reaction equation

HRID 2174956 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:29])[C:13](=[N:26][C:27]#[N:28])[N:14]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([C:24]#[N:25])([CH3:23])[CH3:22])=[CH:17][CH:16]=4)[C:5]=3[C:4]=2[CH:3]=1.[F:30][C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=1[S:38]([NH:41][C:42]1[C:43]([O:57][CH3:58])=[N:44][CH:45]=[C:46](B2OC(C)(C)C(C)(C)O2)[CH:47]=1)(=[O:40])=[O:39].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[C:27]([N:26]=[C:13]1[N:12]([CH3:29])[C:6]2[CH:7]=[N:8][C:9]3[CH:10]=[CH:11][C:2]([C:46]4[CH:47]=[C:42]([NH:41][S:38]([C:32]5[CH:33]=[CH:34][C:35]([F:37])=[CH:36][C:31]=5[F:30])(=[O:40])=[O:39])[C:43]([O:57][CH3:58])=[N:44][CH:45]=4)=[CH:3][C:4]=3[C:5]=2[N:14]1[C:15]1[CH:16]=[CH:17][C:18]([C:21]([C:24]#[N:25])([CH3:22])[CH3:23])=[CH:19][CH:20]=1)#[N:28]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 595647052,4-difluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamideHCID 86683446HCID 86683446, compound

Product 1

HCID 56599239HCID 56599239, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
111 °C

Procedure

To the stirred solution N-(8-bromo-1-(4-(2-cyanopropan-2-yl)phenyl)-3-methyl-1H-imidazo[4,5-c]quinolin-2(3H)-ylidene)cyanamide (0.211 mmol) in dry DMF (5 ml) was added 2,4-difluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide (0.390 mmol) followed by catalyst palladium dichlorobis triphenylphosphine (0.021 mmol). Saturated solution of sodium carbonate (0.780 mmol) was added to it and the resulting solution was heated to 111° C. for 8 minutes in microwave. Solvent was removed and the crude material was extracted in EtOAc, washed with brine several times and dried over anhydrous Na2SO4. The solvent was evaporated and the crude solid was purified (silica gel column, CHCl3/MeOH as eluent) to obtain the title compound.

Workup

  1. customSolvent was removed
  2. extractionthe crude material was extracted in EtOAc
  3. washwashed with brine several times
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was evaporated
  6. customthe crude solid was purified (silica gel column, CHCl3/MeOH as eluent)

Sources & evidence

ORD record
ord-b1b17ec85bc94f0f8d2e3e262d446056
Source dataset
uspto-grants-2015_06
Patent number
US09062046B2

Reaction notes

Loading…