Water → HCID 58238591, compound

HRID 45453Notes

Reaction equation

HRID 45453 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:9][C:10]2[C:15]([CH:16]([CH3:18])[CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=2[CH:19]([CH3:21])[CH3:20])[CH:5]=[CH:6][CH:7]=1.[Li]CCCC.Br[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1.O>C1COCC1.[Cl-].[Cl-].[Zn+2].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH:16]([C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:19]([CH3:20])[CH3:21])[C:10]=1[N:9]=[C:8]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[CH:3]=1)([CH3:17])[CH3:18]

Participants

8

Reactant 4

HCID 962WaterHCID 79732-BromopyridineHCID 58238566N-[(3-Bromophenyl)(phenyl)methylene]-2,6-diisopropylanilineHCID 178418339Butyllithium

Product 1

HCID 58238591HCID 58238591, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418851HCID 178418851, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

To a solution of 1.26 g (3.00 mmol) of 17 in 10 mL of THF, 1.20 mL (3.00 mmol) of 2.5 M nBuLi in hexanes was added at −100° C. This reaction mixture was stirred for 1 hr at −70° C., then cooled to −100° C., and 3.20 mL (3.20 mmol) of 1.0 M ZnCl2 in THF was added. The resulting mixture was slowly warmed to room temperature, stirred for 12 hr at this temperature, and then 0.474 g (3.00 mmol) of 2-bromopyridine and 30 mg (0.06 mmol) of Pd(PtBu3)2 were added. The resulting mixture was refluxed for 3 hr, and 2 mL of water was added. This mixture was passed through short layer of silica gel 60 (40-63 um), and the silica gel layer was additionally washed with 30 mL of dichloromethane. The combined organic elute was evaporated to dryness, and the product was isolated from the residue by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether=10:1, vol.) to generate 1.10 g (88%) of the product.

Workup

  1. temperaturecooled to −100° C.
  2. temperatureThe resulting mixture was slowly warmed to room temperature
  3. stirringstirred for 12 hr at this temperature
  4. temperatureThe resulting mixture was refluxed for 3 hr
  5. washthe silica gel layer was additionally washed with 30 mL of dichloromethane
  6. washThe combined organic elute
  7. customwas evaporated to dryness
  8. customthe product was isolated from the residue by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether=10:1, vol.)

Sources & evidence

ORD record
ord-3ef8b6a2308844a8b4180d93729b018e
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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