Water → HCID 68617428, compound

HRID 2373147Notes

Reaction equation

HRID 2373147 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[CH:36]=[CH:35][C:13]([N:14]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH2:33][CH3:34])=[CH:27][CH:26]=3)[C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH3:24])=[CH:17][CH:16]=3)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].[CH:43]1[C:56]2[NH:55][C:54]3[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=3)[S:48][C:47]=2[CH:46]=[CH:45][CH:44]=1.O>C1(C)C=CC=CC=1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:21]([C:18]1[CH:17]=[CH:16][C:15]([N:14]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH2:33][CH3:34])=[CH:27][CH:26]=2)[C:13]2[CH:35]=[CH:36][C:10]([CH:9]=[CH:8][C:5]3[CH:6]=[CH:7][C:2]([N:55]4[C:56]5[CH:43]=[CH:44][CH:45]=[CH:46][C:47]=5[S:48][C:49]5[C:54]4=[CH:53][CH:52]=[CH:51][CH:50]=5)=[CH:3][CH:4]=3)=[CH:11][CH:12]=2)=[CH:20][CH:19]=1)[CH2:22][CH2:23][CH3:24]

Participants

8

Reactant 4

HCID 962WaterHCID 7108PhenothiazineHCID 23676156Sodium t-butoxideHCID 86600087HCID 86600087, compound

Product 1

HCID 68617428HCID 68617428, compound

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of tris(dibenzylideneacetone) dipalladium (Pd2(dba)3) (0.13 g, 0.14 mmol) and bis(diphenylphosphino)ferrocene (DPPF) (0.10 g, 0.17 mmol) in dry toluene (20 ml) under nitrogen atmosphere was added 4-[2-(4-bromophenyl)vinyl]-N, N-bis(4-butylphenyl)aniline (2.60 g, 4.83 mmol) at room temperature, and the resultant mixture was stirred for 10 min. Sodium tert-butoxide (1.3 g) and phenothiazine (0.96 g, 4.83 mmol) were then added to this solution, which was then stirred at 90° C. overnight under nitrogen. The reaction mixture was poured into water (60 ml), extracted three times with ether (100 ml×3) and dried over anhydrous magnesium sulfate. The product was purified by flash column chromatography using 2% ethyl acetate in hexane as eluant and was isolated in 60% (1.91 g) yield as a yellow solid.

Workup

  1. extractionextracted three times with ether (100 ml×3)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe product was purified by flash column chromatography
  4. customwas isolated in 60% (1.91 g)
  5. customyield as a yellow solid

Sources & evidence

ORD record
ord-9b629f2a3fed4e4a9ee786558ad440a3
Source dataset
uspto-grants-2008_12
Patent number
US07459106B2

Reaction notes

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