Methanol → HCID 10150867, compound

HRID 2376612Notes

Reaction equation

HRID 2376612 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][N:8]=[N:9]3)=[CH:4][C:3]=2[O:2]1.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CO>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[C:10](=[N:9][N:8]=3)[CH:11]=[C:12]3[O:13][CH2:1][O:2][C:3]3=[CH:4]4)[N:14]([CH2:28][CH2:29][CH2:30][CH3:31])[C:15](=[O:27])[C:16]=2[CH:21]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 80271Tri-o-tolylphosphineHCID 69267066HCID 69267066, compound

Product 1

HCID 10150867HCID 10150867, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(6,7-Methylenedioxycinnolin-4-yl)-N-(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 chlorofomm:methanol to provide the title compound (123 mg, 0.2 mmol) in 27% yield with a reaction time 90 min; mp 299° C.; IR (KBr) 1654; 1H NMR (CDCl3) δ 1.06 (t, 3H, J=7.4), 1.56 (m, 2H), 2.13 (m, 2H), 4.09 (s, 3H), 4.17 (s, 3H), 4.49 (m, 2H), 6.26 (s, 2H), 7.62 (s, 1H), 7.85 (s, 1H), 7.87 (s, 1H), 8.65 (s, 1H); 13C NMR (CDCl3) δ 13.8, 20.2, 31.1, 48.6, 56.3, 56.6, 98.8, 102.7, 104.2, 106.5, 107.9, 119.7, 149.1, 150.1, 150.9, 151.4, 153.6, 154.2, 162.9; HRMS calcd for C22H21N3O5H, 408.1559; found 408.1543

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 using chlorofomm

Sources & evidence

ORD record
ord-b74ac29053ea4e40aa22f3b1de6a6c9a
Source dataset
uspto-grants-2008_12
Patent number
US07468366B2

Reaction notes

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