Benzylamine → HCID 67163569, compound

HRID 552756Notes

Reaction equation

HRID 552756 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@H:13]([CH2:14][O:15][Si](C(C)(C)C)(C)C)[O:12][C@@H:11]([N:23]2[C:31]3[CH:30]=[CH:29][N:28]=[C:27](Cl)[C:26]=3[CH:25]=[CH:24]2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:33]([NH2:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CC(C)([O-])C.[Na+]>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].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.O1CCOCC1>[CH2:33]([NH:40][C:27]1[C:26]2[CH:25]=[CH:24][N:23]([C@@H:11]3[O:12][C@H:13]([CH2:14][OH:15])[C@@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])[CH2:10]3)[C:31]=2[CH:30]=[CH:29][N:28]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 3

HCID 7504BenzylamineHCID 23676156Sodium t-butoxideHCID 86607330HCID 86607330, compound

Product 1

HCID 67163569HCID 67163569, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 27342162-(Dicyclohexylphosphino)biphenylCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

A flame dried Schlenk flask was charged with 1-[(2R,4S,5R)-4-{[tert-butyl(dimethyl)silyl]oxy}-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-2-yl]-4-chloro-1H-pyrrolo[3,2-c]pyridine (0.343 g, 0.690 mmol), 1,4 dioxane (1.40 mL), benzylamine (0.226 mL, 2.07 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.0126 g, 0.0138 mmol), 2-(dicyclohexylphosphino)biphenyl (0.00686 g, 0.0196 mmol), and sodium tert-butoxide (0.186 g, 1.93 mmol). The tube purged with N2 (3×), sealed and the mixture was heated at 95° C. overnight. The reaction mixture was cooled to r.t., diluted with CH2Cl2 (20 mL) and washed with water (20 mL). The aq layer was extracted with CH2Cl2 (3×20 mL) and the combined organics were dried (Na2SO4), filtered, and concentrated. The crude oil was purified by flash chromatography (10 to 40% EtOAc/hexanes) to give the title compound as a light yellow foam (0.313 g, 28%).

Workup

  1. customA flame dried Schlenk flask
  2. customThe tube purged with N2 (3×)
  3. customsealed
  4. temperatureThe reaction mixture was cooled to r.t.
  5. additiondiluted with CH2Cl2 (20 mL)
  6. washwashed with water (20 mL)
  7. extractionThe aq layer was extracted with CH2Cl2 (3×20 mL)
  8. dry with materialthe combined organics were dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude oil was purified by flash chromatography (10 to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ec3344efab4b4c39bf5b173b2242199d
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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