Potassium Phosphate, Tribasic → HCID 22660562, compound

HRID 392777Notes

Reaction equation

HRID 392777 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[CH:5]2.[CH3:20][O:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.[OH-].[OH-].[Pd+2]>[CH3:20][O:21][C:22]1[CH:27]=[C:26]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6]([C:11]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[O:12])=[CH:5]3)[CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2734370(3-Methoxyphenyl)boronic acidHCID 9923162HCID 9923162, compound

Product 1

HCID 22660562HCID 22660562, compoundYield 8.1%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A suspension of (5-Bromo-1H-indol-2-yl)-(4-methyl-piperazin-1-yl)-methanone (Example 3, 0.057 g) in dry toluene (0.5 mL) was treated with Pd(OH)2 (0.001 g) under N2 atmosphere. The resulting mixture was then treated with 3-methoxyphenylboronic acid (0.057 g) and then K3PO4 (0.12 g), and heated at 95° C. for 24 h. The reaction mixture was cooled to ambient temperature and diluted with water (2 mL) and toluene (10 mL). The organic layer was separated and washed with brine (2 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was purified via silica gel chromatography (0-12% methanol/dichloromethane) to give the title compound (0.005 g). 1H NMR (400 MHz, CDCl3): δ 9.96 (br s, 1H), 7.53 (d, J=1.6 Hz, 1H), 7.51 (d, J=1.6 Hz, 1H), 7.35 (t, J=7.9 Hz, 1H), 7.23 (s, 1H), 7.21 (s, 1H), 7.17 (m, 1H), 6.87 (dd, J=2.2, 8.1 Hz, 1H), 6.82 (d, J=1.8 Hz, 1H), 3.99 (br s, 4H), 3.86 (s, 3H), 2.52 (t, J=4.9 Hz, 4H), 2.35 (s, 3H). MS (electrospray): exact mass calculated for C21H23N3O2, 349.18; m/z found, 350.2 [M+H]+.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine (2 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified via silica gel chromatography (0-12% methanol/dichloromethane)

Sources & evidence

ORD record
ord-abd1fb1c2ae8416f984dc47ecac2787f
Source dataset
uspto-grants-2004_10
Patent number
US06803362B2

Reaction notes

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