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2-Fluoro-5-iodopyridine → HCID 16748705, compound

HRID 914753
Notes
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Reaction equation

HRID 914753 reaction equation
[C@H:1]12[CH2:7][C@H:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[F:15][C:16]1[CH:21]=[CH:20][C:19](I)=[CH:18][N:17]=1.COC1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[Na+]>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].C(OCC)C>[F:15][C:16]1[N:17]=[CH:18][C:19]([N:5]2[CH2:6][C@@H:1]3[CH2:7][C@H:4]2[CH2:3][N:2]3[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:20][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 27831792-Fluoro-5-iodopyridineHCID 4190002(2'-Methoxy-1,1'-binaphthalen-2-yl)(diphenyl)phosphineHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptaneHCID 23676156Sodium t-butoxide

Product 1

HCID 16748705HCID 16748705, compoundYield 32.1%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 1140TolueneSolvent
HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.300 g, 1.01 mmol), prepared as described in (J. Med. Chem., (1988) 31, 1598-1611), in anhydrous toluene (30 ml) was treated with 2-fluoro-5-iodopyridine (0.34 g, 1.52 mmol), available as described in (U.S. Pat. No. 5,733,912), Pd2(dba)3 (0.028 g, 0.03 mmol), (S)-(−)-2-(diphenylphosphino)-2′-methoxy-1,1′-binaphthyl (0.028 g, 0.06 mmol), available from Strem Chemicals, and sodium tert-butoxide (0.248 g, 2.58 mmol). The reaction mixture was heated at 80° C. for 5 hours. The reaction mixture was poured into diethyl ether (100 mL), washed with brine (100 ml), dried (MgSO4), and concentrated under reduced pressure. The residue was purified by chromatography on SiO2 (3% MeOH/CH2Cl2) to provide the title compound (0.095 g, 21% yield) as a yellow oil. MS (DCI/NH3) m/z 276 (M+H)+.

Workup

  1. washwashed with brine (100 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography on SiO2 (3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-c3c6d36e5c3c445fa8d85a05b0fad08c
Source dataset
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07265115B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes