HCID 86687575, compound → HCID 86687574, compound

HRID 1473519Notes

Reaction equation

HRID 1473519 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])=[CH:9][CH:8]=[C:7]([S:20]([N:23]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)[C:24]1[S:25][CH:26]=[CH:27][N:28]=1)(=[O:22])=[O:21])[CH:6]=2.[C:38]([Zn]C#N)#[N:39]>[Zn].C([Pt](CCCC)CCCC)CCC.[Pd]>[C:38]([C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])=[CH:9][CH:8]=[C:7]([S:20]([N:23]([CH2:29][C:30]1[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=1)[C:24]1[S:25][CH:26]=[CH:27][N:28]=1)(=[O:21])=[O:22])[CH:6]=2)#[N:39]

Participants

5

Reactant 2

HCID 86687575HCID 86687575, compoundHCID 178514179HCID 178514179, compound

Product 1

HCID 86687574HCID 86687574, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 178448207HCID 178448207, compoundCatalyst

Procedure

A vial was charged with 3-bromo-N-(4-methoxybenzyl)-4-(2-methoxyphenyl)-N-(thiazol-2-yl)quinoline-7-sulfonamide (64.6 mg, 0.108 mmol), dicyanozinc (63.6 mg, 0.541 mmol), a spatula tip of zinc dust, and palladium compound with tributylplatinum (1:2) (18.18 mg, 0.022 mmol). The vial was flushed with Ar (g), then DMAC (1 mL) was added. The vial was sealed and placed in a 100° C. heating bath for 4 h. The mixture was cooled to room temperature, and then diluted with water and EtOAc. The layers were separated, and the aq. layer was extracted with EtOAc (2×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (12-g Redi-Sep Gold column, 20-70% EtOAc/Heptane) to give 3-cyano-N-(4-methoxybenzyl)-4-(2-methoxyphenyl)-N-(thiazol-2-yl)quinoline-7-sulfonamide an off-white solid. m/z (ESI) 543.0 (M+H)+.

Workup

  1. customThe vial was flushed with Ar (g)
  2. additionDMAC (1 mL) was added
  3. customThe vial was sealed
  4. customplaced in a 100° C.
  5. temperatureheating bath for 4 h
  6. additiondiluted with water and EtOAc
  7. customThe layers were separated
  8. extractionthe aq. layer was extracted with EtOAc (2×)
  9. dry with materialThe combined organic extracts were dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by chromatography on silica gel (12-g Redi-Sep Gold column, 20-70% EtOAc/Heptane)

Sources & evidence

ORD record
ord-62b69d94c8334a558fbab302b1755dec
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

Loading…