Dimethylformamide → HCID 58275375, compound

HRID 42339Notes

Reaction equation

HRID 42339 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])=[O:9])=[CH:4][C:3]=1[CH3:16].[CH3:17][N:18](C=O)C>CCOC(C)=O.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:12]([NH:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([C:17]#[N:18])=[C:3]([CH3:16])[CH:4]=1)(=[O:10])=[O:9])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 79380454-bromo-N-tert-butyl-3-methylbenzenesulfonamide

Product 1

HCID 58275375HCID 58275375, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-bromo-N-tert-butyl-3-methylbenzenesulfonamide (1.207 g) and zinc cyanide (0.976 g) in DMF (8 ml) was purged with N2 for 20 min. Then PdCl2(dppf) was added. The reaction mixture was heated at 120° C. for 4 hours and showed no reaction. Pd(PPh3)4 was added and the reaction mixture was stirred at 120° C. over the weekend. The reaction mixture was diluted with EtOAc and washed with 5% LiCl solution (2×). The combined organic layers were dried (MgSO4), concentrated and purified by silica gel column chromatography to give 1.227 g N-tert-butyl-4-cyano-3-methylbenzenesulfonamide as a white solid.

Workup

  1. customwas purged with N2 for 20 min
  2. additionThen PdCl2(dppf) was added
  3. customno reaction
  4. washwashed with 5% LiCl solution (2×)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-18167941bf1d446eaa96745709fedbc5
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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