HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Pyrrolidine → 3-Bromo-5-(pyrrolidin-1-yl)pyridine

HRID 573599
Notes
Print preview

Reaction equation

HRID 573599 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.CC(C)([O-])C.[Na+].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 31268PyrrolidineHCID 693693,5-DibromopyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 467395273-Bromo-5-(pyrrolidin-1-yl)pyridineYield 75.9%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-Catalyst
HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3,5-dibromopyridine (5.5 g, 23.22 mmol) in toluene (100 mL) was added BINAP (0.840 g, 1.350 mmol), Pd2(dba)3 (0.412 g, 0.45 mmol), sodium tert-butoxide (6.49 g, 67.5 mmol) and pyrrolidine (1.86 mL, 22.50 mmol). The reaction mixture was degassed (N2, 10 min) and then heated at 100° C. for 2 h. The reaction mixture was cooled to RT and filtered through celite. The filtrate was evaporated and the residue purified by silica gel chromatography, eluting with a gradient of 0-30% ethyl acetate in cyclohexane, to afford the title compound (3.88 g). LCMS (A) m/z: 227/229 [M+1]+, Rt 0.87 min (acidic),

Workup

  1. customThe reaction mixture was degassed (N2, 10 min)
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationfiltered through celite
  4. customThe filtrate was evaporated
  5. customthe residue purified by silica gel chromatography
  6. washeluting with a gradient of 0-30% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-3fa8a146c40346b68a0a204e0b03e7fc
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09029545B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes