Potassium Carbonate → 2-Amino-5-[4-[3-(aminosulfonyl)phenyl]-6-quinolinyl]-3-pyridinesulfonamide

HRID 1625953Notes

Reaction equation

HRID 1625953 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2Cl.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].[NH2:36][C:37]1[C:42]([S:43]([NH2:46])(=[O:45])=[O:44])=[CH:41][C:40](Br)=[CH:39][N:38]=1.C(=O)([O-])[O-].[K+].[K+].CC1(C)C(C)(C)OB([C:62]2[CH:63]=[C:64]([S:68]([NH2:71])(=[O:70])=[O:69])[CH:65]=[CH:66][CH:67]=2)O1>O1CCOCC1.[Pd].C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[NH2:36][C:37]1[C:42]([S:43]([NH2:46])(=[O:45])=[O:44])=[CH:41][C:40]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][CH:6]=[C:5]3[C:62]2[CH:67]=[CH:66][CH:65]=[C:64]([S:68]([NH2:71])(=[O:70])=[O:69])[CH:63]=2)=[CH:39][N:38]=1

Participants

10

Reactant 6

HCID 11430Potassium Carbonate2×HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 51395376-Bromo-4-chloroquinolineHCID 164142303-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamideHCID 523351762-Amino-5-bromopyridine-3-sulfonamide

Product 1

HCID 598601872-Amino-5-[4-[3-(aminosulfonyl)phenyl]-6-quinolinyl]-3-pyridinesulfonamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 53485975CID 53485975Catalyst2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

This compound was prepared in one pot (three steps) with no workups between steps. A mixture of 6-bromo-4-chloroquinoline, (484 mg, 2 mmol), bis(pinacolato)diboron, (506 mg, 2 mmol), dichloro-[1,1′bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (81.5 mg, 0.1 mmol), and potassium acetate (588 mg, 6 mmol) in dioxane (6 mL) was heated at 100° C. for 4 h. To this reaction was added 2-amino-5-bromo-3-pyridinesulfonamide, (560 mg 2 mmol) an equal amount of the palladium catalyst used above (0.1 mmol) and 2 M potassium carbonate (3 mL). The reaction was heated at 95 deg centigrade for one hour. To this reaction was added 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide, (566 mg 2 mmol), dichloro-[1,1′bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (81.5 mg, 0.1 mmol) and 2 M potassium carbonate (3 mL). The reaction was heated at 95° C. for three hours. The solvent was evaporated and the crude material purified by silica gel chromatography, eluting with ethyl acetate. The product was purified further by crystallizing from hot ethyl acetate. Obtained 181 mg (18.7%) for three steps. MS(ES)+ m/e 484 [M+H]+.

Workup

  1. customThis compound was prepared in one pot (three steps) with no workups between steps
  2. temperatureThe reaction was heated at 95 deg centigrade for one hour
  3. temperatureThe reaction was heated at 95° C. for three hours
  4. customThe solvent was evaporated
  5. customthe crude material purified by silica gel chromatography
  6. washeluting with ethyl acetate
  7. customThe product was purified further
  8. customby crystallizing from hot ethyl acetate
  9. customObtained 181 mg (18.7%) for three steps

Sources & evidence

ORD record
ord-c44db18eba154441ab55146c7eb88103
Source dataset
uspto-grants-2014_07
Patent number
US08785433B2

Reaction notes

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