2-(Tributylstannyl)furan → HCID 178441006, compound

HRID 747855Notes

Reaction equation

HRID 747855 reaction equation
[C:1]([C:5]1[CH:35]=[CH:34][C:8]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH2:20][C:21]3[CH:22]=[N:23][C:24]([O:32]C)=[C:25]([C:27]4[O:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=3)=[N:12][N:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(C1C=CC(NC2C3C(=CC=CC=3)C(CC3C=NC(OC)=C(Br)C=3)=NN=2)=CC=1)(C)(C)C.C([Sn](CCCC)(CCCC)C1OC=CC=1)CCC>CCOC(C)=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH2:20][C:21]3[CH:22]=[N:23][C:24]([OH:32])=[C:25]([C:27]4[O:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=3)=[N:12][N:11]=2)=[CH:34][CH:35]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 43936882-(Tributylstannyl)furanHCID 67215339HCID 67215339, compoundHCID 67215494HCID 67215494, compound

Product 1

HCID 178441006HCID 178441006, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

1-(4-tert-Butyl-anilino)4[5-(furan-2-yl)-6-methoxy-(pyridin-3-yl)-methyl]phthalazine: To a solution of 366 mg (0.76 mMol) 1-(4-tert-butyl-anilino)-4-[5-bromo-6-methoxy-(pyridin-3-yl)-methyl]phthalazine (Ex. 17: a) In 7 ml degassed DMF under a N2-atmoshere are added 174 mg (0.15 mMol) of Pd[P(C8H5)3]4 and 0.6 ml (1.9 mMol) of 2-tributylstannyl-furan (Aldrich). After 4 h stirring at 100° C., the reaction mixture is diluted with EtOAc and washed with NaHCO3 solution. The aqueous layers are extracted twice with EtOAc, the organic phases washed with water, brine, dried (Na2SO4) and concentrated in vacuuo. Column chromatography (SiO2; CH2Cl2/Et2O 7:3) and cristalization from DIPE yields the title compound. mp: 180-182° C.; ES-MS: (M+H)+=465; HPLC(Grad20-100) tRet=15.0.

Workup

  1. custom17: a) In 7 ml degassed DMF under a N2-atmoshere
  2. washwashed with NaHCO3 solution
  3. extractionThe aqueous layers are extracted twice with EtOAc
  4. washthe organic phases washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuuo

Sources & evidence

ORD record
ord-986bd5ea2de24aec840d181961894982
Source dataset
uspto-grants-2008_07
Patent number
US07399761B2

Reaction notes

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