4-(Tri-n-butylstannyl)pyridine → 1,2,3,4-Tetrahydro-2-[5-(4-pyridinyl)-pyrimidin-2-yl]-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one

HRID 988326Notes

Reaction equation

HRID 988326 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:20][C:19]3[C:18](=[O:21])[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[NH:11][C:10]=3[CH:9]2[C:22]2[CH:27]=[CH:26][C:25]3[O:28][CH2:29][O:30][C:24]=3[CH:23]=2)=[N:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:36]1[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=1)CCC>CN(C=O)C.C(OCC)(=O)C.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>[N:39]1[CH:40]=[CH:41][C:36]([C:2]2[CH:3]=[N:4][C:5]([N:8]3[CH2:20][C:19]4[C:18](=[O:21])[C:17]5[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=5[NH:11][C:10]=4[CH:9]3[C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][O:30][C:24]=4[CH:23]=3)=[N:6][CH:7]=2)=[CH:37][CH:38]=1

Participants

6

Reactant 2

HCID 27373184-(Tri-n-butylstannyl)pyridineHCID 129930361,2,3,4-Tetrahydro-2-(5-bromopyrimidin-2-yl]-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one

Product 1

HCID 129930371,2,3,4-Tetrahydro-2-[5-(4-pyridinyl)-pyrimidin-2-yl]-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A stirred mixture of 1,2,3,4-tetrahydro-2-(5-bromopyrimidin-2-yl)-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one (46 mg, 0.1 mmol) (prepared as in Example 53), (PPh3)4Pd (3.5 mg, 3.0 μmol) and 4-tri-n-butylstannylpyridine (37 mg, 0.1 mmol) in dry DMF (2.0 ml) was heated at 140° C. for 12 h. More catalyst (3.5 mg) was added and the mixture was refluxed for 4 h and then cooled. The solution was diluted with ethyl acetate and filtered through filter paper. The organic phase was washed with brine and water, then dried over Na2SO4. A small amount of silica gel was added into the solution and dried in vacuo. Purification by flash column (silica gel, neat acetonitrile followed by 10% ammonium hydroxide in water:actonitrile=1:10, v/v) yielded the product as a white solid.

Workup

  1. temperaturethe mixture was refluxed for 4 h
  2. temperaturecooled
  3. filtrationfiltered
  4. filtrationthrough filter paper
  5. washThe organic phase was washed with brine and water
  6. dry with materialdried over Na2SO4
  7. additionA small amount of silica gel was added into the solution
  8. customdried in vacuo
  9. customPurification by flash column (silica gel, neat acetonitrile

Sources & evidence

ORD record
ord-69990a0b6ea64410ada3b0a3383c57d4
Source dataset
uspto-grants-2003_10
Patent number
US06635638B2

Reaction notes

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