4-Bromopyridinium chloride → HCID 69272331, compound

HRID 751530Notes

Reaction equation

HRID 751530 reaction equation
[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH2:15][CH2:14]2)([CH3:4])([CH3:3])[CH3:2].Cl.Br[C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.CC(C)([O-])C.[Na+]>O1CCOCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[N:16]([C:30]1[CH:29]=[CH:28][CH:33]=[CH:32][N:31]=1)[CH2:15][CH2:14]2)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 881004-Bromopyridinium chlorideHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 69272023HCID 69272023, compound

Product 1

HCID 69272331HCID 69272331, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Bubble nitrogen through benzyl-(2,3-dihydro-1H-indol-7-ylmethyl)carbamic acid tert-butyl ester (3.7 g, 10.9 mmol) in 1,4-dioxane (50 mL) in a sealed tube. Mix with 4-bromopyridine hydrochloride (4.3 g, 21.9 mmol), palladium diacetate (0.5 g, 2.18 mmol), 2-(dicyclohexylphosphino)biphenyl (0.76 g, 2.18 mmol) and sodium tert-butoxide (3.1 g, 32.7 mmol). Stir the mixture 110° C. for 16 hours. Cool and filter, then concentrate the filtrate. Purify by chromatography (silica gel; hexane/ethyl acetate; 3:1 to 0:1) to isolate a solid as the title compound (1.5 g, 33%). MS (ESI) m/z 416 (M+H)+.

Workup

  1. temperatureCool
  2. filtrationfilter
  3. concentrationconcentrate the filtrate
  4. customPurify by chromatography (silica gel; hexane/ethyl acetate; 3:1 to 0:1)

Sources & evidence

ORD record
ord-31ee03c9260d4e5ba8f51f496e669b1c
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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