Water → HCID 22381652, compound

HRID 2373145Notes

Reaction equation

HRID 2373145 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].CC(C)([O-])C.[Na+].[CH:18]1[C:31]2[NH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[S:23][C:22]=2[CH:21]=[CH:20][CH:19]=1.O>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].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]>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([N:30]2[C:31]3[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=3[S:23][C:24]3[C:29]2=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 962WaterHCID 7108PhenothiazineHCID 5210591-Bromo-4-butylbenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 22381652HCID 22381652, compound

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of tris(dibenzylideneacetone)dipalladium (Pd2(dba)3) (0.30 g, 0.33 mmol) and bis(diphenylphosphino)ferrocene (DPPF) (0.22 g, 0.40 mmol) in dry toluene (60 ml) under nitrogen atmosphere was added 4-(butyl)phenylbromide (3.21 g, 15.1 mmol) at room temperature, and the resultant mixture was stirred for 10 min., sodium tert-butoxide (4.0 g) and phenothiazine (3.0 g, 15.1 mmol) were added to this solution and stirred at 90° C. overnight under nitrogen. The reaction mixture was poured into water (80 ml), extracted three times with ether (100 ml×3) and dried over anhydrous magnesium sulfate. The product was purified by flash column chromatography using 5% ethyl acetate in hexane as eluant and was isolated in 81% (4.03 g) yield as a pale yellow solid.1H NMR (CDCl3, 500 MHz) δppm: 7.41 (d, J=7.0 Hz, 2H), 7.29 (d, J=8.0 Hz, 2H), 7.0 (dd, J=7.5 Hz, J=1.5 Hz, 2H), 6.7-6.9 (m, 4H), 6.20 (d, J=7.5 Hz, 2H), 2.72 (t, J=7.5 Hz, 2H, CH2), 1.7 (m, 2H, CH2), 1.44 (m, 2H, CH2), 0.99 (t, J=7.0 Hz, 3H, CH3).

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 81% (4.03 g)
  5. customyield as a pale yellow solid

Sources & evidence

ORD record
ord-ce7fd60a48d042c0b02c241060fac370
Source dataset
uspto-grants-2008_12
Patent number
US07459106B2

Reaction notes

Loading…