Dichloromethane → HCID 68323804, compound

HRID 573610Notes

Reaction equation

HRID 573610 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:22])=[CH:8][C:9]=2[NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)(=[O:14])=[O:13])[S:4][C:3]=1[CH3:23].[CH3:24][N:25]([CH3:35])[C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1.C(Cl)Cl.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[Cl:21][C:17]1[CH:16]=[C:15]([S:12]([NH:11][C:9]2[CH:8]=[C:7]([CH3:22])[N:6]=[C:5]3[S:4][C:3]([CH3:23])=[C:2]([C:30]4[CH:29]=[CH:28][CH:27]=[C:26]([N:25]([CH3:35])[CH3:24])[CH:31]=4)[C:10]=23)(=[O:14])=[O:13])[CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 27625273-(Dimethylamino)benzeneboronic acidHCID 68324076N-(3-bromo-2,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide

Product 1

HCID 68323804HCID 68323804, compoundYield 36.1%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

Under nitrogen, N-(3-bromo-2,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide (100 mg, 0.232 mmol) (Example 61) was dissolved in toluene (2 mL) and [3-(dimethylamino)phenyl]boronic acid (57.3 mg, 0.347 mmol), PdCl2(dppf).DCM (18.91 mg, 0.023 mmol) and Cs2CO3 (226 mg, 0.695 mmol) were added and the mixture heated in a microwave at 150° C. for 30 min. Water (10 mL) was then added and the mixture extracted with ethyl acetate (3×10 mL). The organic layer was dried over MgSO4, filtered and the solvent removed in vacuo. Purification by chromatography on silica gel, eluting with a gradient of 0-30% ethyl acetate in cyclohexane, was followed by trituration with MeOH, to afford the title compound (39.5 mg). LCMS (A) m/z: 472 [M+1]+, Rt 0.97 min (basic), Rt 1.51 min (acidic).

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×10 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customPurification by chromatography on silica gel
  6. washeluting with a gradient of 0-30% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-c366ac03f52d4c16bbf92611874bbd2b
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

Loading…