1,4-Dioxane → HCID 57551245, compound

HRID 1644653Notes

Reaction equation

HRID 1644653 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[C:4]([C:17]#[N:18])[CH:3]=1.CC(C)([O-])C.[Na+].[CH3:25][C:26]1([CH3:66])[C:39]2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)[C:34]=2OC2[C:27]1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.[NH2:67][C:68]1[S:69]C=C(C2C=CC(Cl)=CC=2)[N:72]=1.O1CCOCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:26]([C:39]1[N:67]=[C:68]([NH:72][C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]3[S:13][CH:14]=[CH:15][N:16]=3)(=[O:10])=[O:9])=[C:4]([C:17]#[N:18])[CH:3]=2)[S:69][CH:34]=1)([CH3:66])([CH3:27])[CH3:25]

Participants

7

Reactant 5

HCID 312751,4-DioxaneHCID 732412-Amino-4-(4-chlorophenyl)thiazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 57551218HCID 57551218, compound

Product 1

HCID 57551245HCID 57551245, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
150 °C

Procedure

Into a Vial was added the 4-Bromo-2-cyano-N-thiazol-2-yl-benzenesulfonamide (35 mg, 0.00010 mol), Sodium tert-butoxide (29 mg, 0.00030 mol), 9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE (7.1 mg, 0.000012 mol), Tris(dibenzylideneacetone)dipalladium(0) (3.7 mg, 0.0000041 mol), 2-AMINO-4-(4-CHLOROPHENYL)THIAZOLE and the de-gassed anhydrous 1,4-Dioxane (1.4 mL, 0.018 mol). The reaction mixture was heated at 150° C. for 1 h in microwave. The reaction mixture was filtered through celite and the filtrate was concentrated. The residue was diluted with ethyl acetate and washed with 1.0 N HCl, dried and was concentrated to give the crude product that was purified on ISCO twice (10% methanol in chloroform for first run, 25% Ethyl acetate to 100% Ethyl acetate for second run). Product was lyophilized from acetonitrile-water to afford a light orange powder.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with 1.0 N HCl
  5. customdried
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-b6dcf79ee4d5429fad404c6b1af58534
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

Loading…