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

3,5-Dibromopyridine → (3aR,6aS)-tert-butyl 5-(5-bromopyridin-3-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

HRID 240499
Notes
Print preview

Reaction equation

HRID 240499 reaction equation
[CH2:1]1[C@@H:5]2[CH2:6][NH:7][CH2:8][C@@H:4]2[CH2:3][N:2]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[Br:16][C:17]1[CH:18]=[N:19][CH:20]=[C:21](Br)[CH:22]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.O.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:16][C:17]1[CH:22]=[C:21]([N:7]2[CH2:6][C@@H:5]3[CH2:1][N:2]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3][C@@H:4]3[CH2:8]2)[CH:20]=[N:19][CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 693693,5-DibromopyridineHCID 1514452Cis-2-boc-hexahydropyrrolo[3,4-C]pyrroleHCID 23676156Sodium t-butoxide

Product 1

HCID 44189936(3aR,6aS)-tert-butyl 5-(5-bromopyridin-3-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylateYield 67%

Reagents, catalysts & solvents 4

HCID 634876
Binap, (A+-)-
Catalyst
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 962WaterSolvent
HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

The product from Example 1C (1.01 g, 4.76 mmol) and 3,5-dibromopyridine (1.22 g, 5.15 mmol) were dissolved in toluene (20 mL). Pd2(dba)3 (86.8 mg, 0.095 mmol), BINAP (175.0 mg, 0.28 mmol) and sodium tert-butoxide (665.4 mg, 1.460 mmol) were added to the reaction mixture. The reaction was heated to 80° C. for 22 h, then allowed to cool to ambient temperature, diluted with water (100 mL) and extracted with CH2Cl2 (3×100 mL). The organic extracts were combined and washed with brine (50 mL), dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by silica gel chromatography (EtOAc, Rf=0.33) to afford the title compound as a white solid (1.17 g, 67%). MS (DCI/NH3) m/z 370 (M+H)+.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionextracted with CH2Cl2 (3×100 mL)
  3. washwashed with brine (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by silica gel chromatography (EtOAc, Rf=0.33)

Sources & evidence

ORD record
ord-bc45a253e46b4974b20a230d5b57e4b4
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08648084B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes