Cesium carbonate → HCID 136611525, compound

HRID 2173034Notes

Reaction equation

HRID 2173034 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1/[C:7](=[N:9]/[N:10]=[C:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)/[CH3:8].[C:24]1([C:30](=[N:37][NH2:38])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:12]1([C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:10]/[N:9]=[C:7](/[C:3]2[S:4][CH:5]=[CH:6][C:2]=2[NH:38][N:37]=[C:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)\[CH3:8])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 79304DiphenylmethylidenehydrazineHCID 89330309HCID 89330309, compound

Product 1

HCID 136611525HCID 136611525, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a mixture of (E)-1-(1-(3-bromothiophen-2-yl)ethylidene)-2-(diphenylmethylene)hydrazine (12.5 g, 32.6 mmol, including its Z isomer) and (diphenylmethylene)hydrazine (7.68 g, 39.1 mmol) in toluene (25 mL) was added palladium(II) acetate (0.385 g, 6.52 mmol), 1,1′-bis(diphenylphosphino)ferrocene (1.808 g, 3.26 mmol) and Cs2CO3 (21.25 g, 65.2 mmol). The reaction mixture was heated at 80° C. for 14 hours. The mixture was subsequently diluted with toluene (25 mL) and filtered to remove solids. The filtrate was evaporated and chromatographed using a gradient of 0-100% hexane and EtOAc. The pure product fractions were combined and evaporated to give the title compound (12.5 g, 77%). ESI-MS m/z [M+H]+ calc'd for C32H26N4S, 499. found, 499.

Workup

  1. filtrationfiltered
  2. customto remove solids
  3. customThe filtrate was evaporated
  4. customchromatographed
  5. customevaporated

Sources & evidence

ORD record
ord-a43949f4325145fe9ba399e2c6183b81
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

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