Dichloromethane → 4-[3-(2-chloro-phenyl)-indole-1-sulfonyl]-N-(4-fluoro-benzyl)-benzamide

HRID 1178978Notes

Reaction equation

HRID 1178978 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8](=[O:28])[C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20](I)=[CH:19]3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[Cl:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1B(O)O.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd]Cl.O.CCOC(C)=O.CN(C=O)C>[Cl:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:18]([S:15]([C:12]2[CH:13]=[CH:14][C:9]([C:8]([NH:7][CH2:6][C:5]3[CH:29]=[CH:30][C:2]([F:1])=[CH:3][CH:4]=3)=[O:28])=[CH:10][CH:11]=2)(=[O:17])=[O:16])[CH:19]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 58975061N-(4-fluoro-benzyl)-4-(3-iodo-indole-1-sulfonyl)-benzamide

Product 1

HCID 589750894-[3-(2-chloro-phenyl)-indole-1-sulfonyl]-N-(4-fluoro-benzyl)-benzamideYield 60%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Procedure

Add N-(4-Fluoro-benzyl)-4-(3-iodo-indole-1-sulfonyl)-benzamide (268 mg, 0.0.50 mmol), 2-chlorophenylboronic acid (78.2 mg, 0.50 mmol), PdCl2 (dppf).CH2Cl2 (41 mg, 0.05 mmol) and 2M Na2CO3 (0.55 mL, 1.1 mmol) respectively to DMF (15.0 mL) at ambient temperature under N2. Heat the reaction to 100° C. for 16 h. Cool the reaction to ambient temperature and pour into a H2O-EtOAc mixture (200 mL/100 mL). Separate the EtOAc, extract several times with H2O and wash with brine. Dry (MgSO4), filter and evaporate the filtrate. Purify the crude material on silica gel using a gradient hexane-EtOAc system to give 0.155 g (60% yield) of 4-[3-(2-chloro-phenyl)-indole-1-sulfonyl]-N-(4-fluoro-benzyl)-benzamide: Mass spectrum (m/e)M−1) 517.0787.

Workup

  1. customat ambient temperature
  2. temperatureHeat
  3. customthe reaction to 100° C. for 16 h
  4. temperatureCool
  5. customthe reaction to ambient temperature
  6. customSeparate the EtOAc
  7. extractionextract several times with H2O
  8. washwash with brine
  9. dry with materialDry (MgSO4)
  10. filtrationfilter
  11. customevaporate the filtrate
  12. customPurify the crude material on silica gel using a gradient hexane-EtOAc system

Sources & evidence

ORD record
ord-e09ccd31c18244819a43e7dc688eb9d7
Source dataset
uspto-grants-2007_10
Patent number
US07276516B2

Reaction notes

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