Dichloromethane → HCID 68323762, compound

HRID 573694Notes

Reaction equation

HRID 573694 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][C:25]([C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)([CH3:27])[CH3:26].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:31]4[CH:32]=[CH:33][C:28]([C:25]([CH3:27])([CH3:26])[CH3:24])=[CH:29][CH:30]=4)[C:10]=23)(=[O:14])=[O:13])[CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 27343204-tert-Butylphenylboronic acidHCID 68324076N-(3-bromo-2,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide

Product 1

HCID 68323762HCID 68323762, compoundYield 45.3%

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 (Example 61) (100 mg, 0.232 mmol) was dissolved in toluene (2 mL) and [4-(1,1-dimethylethyl)phenyl]boronic acid (61.9 mg, 0.347 mmol), PdCl2(dppf).DCM (18.91 mg, 0.023 mmol) and Cs2CO3 (226 mg, 0.695 mmol) were added. The mixture was then heated in a microwave at 150° C. for 30 min. Water (10 mL) was added and the mixture extracted with ethyl acetate (3×10 mL). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by normal phase chromatography, eluting with a gradient of 0-20% ethyl acetate in cyclohexane, to give the title compound (51 mg). LCMS (A) m/z: 485 [M+1]+, Rt 1.70 min (basic).

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×10 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by normal phase chromatography
  6. washeluting with a gradient of 0-20% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-a06296bc4eb8430489458693afbd7710
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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