2,5-Dibromopyridine → HCID 11328288, compound

HRID 983420Notes

Reaction equation

HRID 983420 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([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][NH:11]3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.Br[C:24]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][N:25]=1.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:30][C:27]1[CH:28]=[CH:29][C:24]([N:11]2[CH2:12][CH2:13][C:14]3[C:15]4[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=4)[NH:21][C:22]=3[CH:10]2[C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][CH2:3][C:4]=3[CH:9]=2)=[N:25][CH:26]=1

Participants

7

Reactant 4

HCID 693532,5-DibromopyridineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 111090451-(2,3-dihydro-5-benzofuranyl)-2,3,4,9-tetrahydro-1H-beta-carbolineHCID 23676156Sodium t-butoxide

Product 1

HCID 11328288HCID 11328288, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

1-(2,3-dihydro-5-benzofuranyl)-2,3,4,9-tetrahydro-1H-β-carboline (11.6 g, 40 mmol), 2,5-dibromopyridine (10.42 g, 44 mmol), Pd2dba3 (1.465 g, 1.6 mmol), dppp (1.32 g, 3.2 mmol) and NaOtBu (5.38 g, 56 mmol) were stirred in 60 mL DMF at 80° C. for 3 days. The reaction mixture was filtered through a plug of Celite with CH2Cl2. The reaction mixture was then concentrated, the crude mixture was then loaded on Foxy column (110 g silica gel) and eluted with ethyl acetate/hexane (3:7). The product crystallized out in test tubes. The product was concentrated and then recrystallized from THF to yield the product as yellow crystals.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite with CH2Cl2
  2. concentrationThe reaction mixture was then concentrated
  3. washeluted with ethyl acetate/hexane (3:7)
  4. customThe product crystallized out in test tubes
  5. concentrationThe product was concentrated
  6. customrecrystallized from THF

Sources & evidence

ORD record
ord-697379f5162742e7922be66349298588
Source dataset
uspto-grants-2005_03
Patent number
US06864253B2

Reaction notes

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