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Tri-o-tolylphosphine → HCID 10216245, compound

HRID 2376613
Notes
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Reaction equation

HRID 2376613 reaction equation
[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6]([N:14]([CH2:28][CH2:29][CH2:30][CH3:31])[C:15](=[O:27])[C:16]4[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[CH:18][C:17]=4I)=[CH:7][CH:8]=[N:9]3)=[CH:4][C:3]=2[O:2]1.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C=O)C.C(Cl)(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:23][O:22][C:20]1[C:19]([O:24][CH3:25])=[CH:18][C:17]2[C:7]3[C:6](=[C:5]4[CH:4]=[C:3]5[O:2][CH2:1][O:13][C:12]5=[CH:11][C:10]4=[N:9][CH:8]=3)[N:14]([CH2:28][CH2:29][CH2:30][CH3:31])[C:15](=[O:27])[C:16]=2[CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 80271Tri-o-tolylphosphineHCID 69268189HCID 69268189, compound

Product 1

HCID 10216245HCID 10216245, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6212ChloroformSolvent
HCID 6228
Dimethylformamide
Solvent

Procedure

A mixture of the N-(6,7-Methylenedioxyquinolin-4-yl)-N-(butyl)-2-iodo-4,5-dimethoxybenzamide (1.0 mmol equiv.), Pd(OAc)2 (0.2 mmol equiv.), P(o-tolyl)3 (0.4 mmol equiv.), and Ag2CO3 (2.0 mmol equiv) was heated to reflux in DMF (30 mL per mmol equiv.) with stirring. The reaction mixture was allowed to cool to room temperature, diluted with CHCl3, and filtered through Celite. The sicciate was extensively washed with 10% CH3OH in CHCl3. The filtrate was concentrated in vacuo and the residue chromatographed on silica gel using chloroform:methanol to provide the title compound; (24% yield); reaction time 45 min; mp 224° C. (dec.); IR (KBr) 1654; 1H NMR (CDCl3); δ 0.99 (t, 3H, J=7.4), 1.62 (m, 2H), 2.09 (m, 2H), 4.07 (s, 3H), 4.14 (s, 3H), 4.49 (m, 2H), 6.19 (s, 2H), 7.50 (s, 1H), 7.61 (s, 1H), 7.70 (s, 1H), 7.92 (s, 1H), 9.40 (s, 1H); 13C NMR (CDCl3) δ 13.7, 20.2, 31.2, 50.6, 56.3, 56.4, 100.7, 102.0, 102.2, 107.4, 108.8, 111.7, 114.9, 119.5, 127.4, 141.1, 143.7, 147.1, 147.5, 149.8, 150.3, 154.1, 164.0; HRMS calcd for C23H22N2O5H, 406.1529; found 406.1534.

Workup

  1. temperaturewas heated
  2. filtrationfiltered through Celite
  3. washThe sicciate was extensively washed with 10% CH3OH in CHCl3
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-7f75e2caec224ee88ce3191d4375010f
Source dataset
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07468366B2

Reaction notes

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