2-(Tributylstannyl)furan → HCID 67215494, compound

HRID 1663009Notes

Reaction equation

HRID 1663009 reaction equation
[C:1]([C:5]1[CH:31]=[CH:30][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:28][CH3:29])=[C:25](Br)[CH:26]=3)=[N:12][N:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:37]1[O:38][CH:39]=[CH:40][CH:41]=1)CCC>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([C:5]1[CH:31]=[CH:30][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:28][CH3:29])=[C:25]([C:37]4[O:38][CH:39]=[CH:40][CH:41]=4)[CH:26]=3)=[N:12][N:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

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

Product 1

HCID 67215494HCID 67215494, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

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-atmosphere are added 174 mg (0.15 mMol) of Pd[P(C6H5)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 vacuo. Column chromatography (SiO2; CH2Cl2/Et2O 7:3) and crystallization 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-atmosphere
  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 vacuo
  7. customColumn chromatography (SiO2; CH2Cl2/Et2O 7:3) and crystallization from DIPE

Sources & evidence

ORD record
ord-3b083db176c84484ba7b8f8447e33c33
Source dataset
uspto-grants-2011_10
Patent number
US08034814B2

Reaction notes

Loading…