Triethylamine → 1-(3,4-Methylenedioxyphenyl)-2-[5-(3-pyridinyl)-pyrimidin-2-yl)-2,3,4,9-tetrahydro-1H-beta-carboline

HRID 2415386Notes

Reaction equation

HRID 2415386 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23]3[N:28]=[CH:27][C:26](Br)=[CH:25][N:24]=3)=[CH:4][C:3]=2[O:2]1.[N:30]1[CH:35]=[CH:34][CH:33]=[C:32](B(O)O)[CH:31]=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23]3[N:28]=[CH:27][C:26]([C:32]4[CH:31]=[N:30][CH:35]=[CH:34][CH:33]=4)=[CH:25][N:24]=3)=[CH:4][C:3]=2[O:2]1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 27343783-Pyridinylboronic acidHCID 226403241-(3,4-Methylenedioxyphenyl)-2-(5-bromopyrimidin-2-yl)-2,3,4,9-tetrahydro-1H-beta-carboline

Product 1

HCID 226403091-(3,4-Methylenedioxyphenyl)-2-[5-(3-pyridinyl)-pyrimidin-2-yl)-2,3,4,9-tetrahydro-1H-beta-carboline

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A stirred mixture of palladium(II) acetate (27 mg, 0.12 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (dppf) (83 mg, 0.15 mmol) in dry DMF (20 ml) was warmed to 50° C. for 15 min and then cooled. 1-(3,4-methylenedioxyphenyl)-2-(5-bromopyrimidin-2-yl)-2,3,4,9-tetrahydro-1H-β-carboline (674 mg, 1.5 mmol) (prepared as in Example 52), pyridine-3-boronic acid (203 mg, 1.7 mmol) and triethylamine (0.3 ml, 2.1 mmol) were added to the solution and the mixture heated to 90° C. for 16 h. 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 the solution was dried in vacuo. Purification by flash column (silica gel, hexane:ethyl acetate=1:1, v/v, followed by hexane:ethyl acetate=1:2, v/v) yielded the product as a white solid.

Workup

  1. temperaturecooled
  2. temperaturethe mixture heated to 90° C. for 16 h
  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. customthe solution was dried in vacuo
  9. customPurification by flash column (silica gel, hexane

Sources & evidence

ORD record
ord-bd0841c0531c4ad79efe97d063a0f527
Source dataset
uspto-grants-2004_11
Patent number
US06818646B2

Reaction notes

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