Sodium Carbonate → HCID 68434137, compound

HRID 1713938Notes

Reaction equation

HRID 1713938 reaction equation
Br[C:2]1[N:3]([CH2:21][C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2.ClCC(N(C)C)=O.C([O-])([O-])=O.[Na+].[Na+].[CH3:40][O:41][C:42]1[CH:47]=[CH:46][C:45](B(O)O)=[CH:44][N:43]=1>O1CCOCC1>[CH:11]1([C:10]2[C:9]3[C:4](=[CH:5][C:6]([C:17]([O:19][CH3:20])=[O:18])=[CH:7][CH:8]=3)[N:3]([CH2:21][C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[C:2]=2[C:45]2[CH:44]=[N:43][C:42]([O:41][CH3:40])=[CH:47][CH:46]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 21105286HCID 21105286, compound

Product 1

HCID 68434137HCID 68434137, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 2-bromo-3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-1H-indole-6-carboxylate (1 eq), prepared as described in Example 3, Step 1, but using 2-chloro-N,N-dimethylacetamide in the alkylation step, in dioxane (0.06 M) was added bistriphenylphosphine-palladium dichloride (0.2 eq). The reaction mixture was left at RT under nitrogen atmosphere for 15 min, at that rime an aqueous solution of Na2CO3 (2 M), (2.93 eq) and 2-methoxy-5-pyridineboronic acid (2.5 eq) were added. The reaction mixture was heated to reflux for 2 h, then was cooled to RT and concentrated in vacuo. The residue was diluted with DCM, filtered and washed with water, brine, dried over Na2SO4, filtered and evaporated in vacuo to give the title compound (85%). 1H NMR (400 MHz; DMSO-d6, 300 K) δ 1.20-1.28 (m, 3H), 1.65-1.85 (m, 7H), 2.50-2.54 (m, 1H), 2.8 (s, 3H), 2.9 (s, 3H), 3.87 (s, 3H), 3.93 (s, 3H), 4.92 (s, 2H), 6.97 (d, J 8.4, 1H), 7.62 (d, J 8.8, 1H), 7.67 (d, J 8.8, 1H), 7.85 (d, J 8.4, 1H), 7.99 (s, 1H), 8.11 (s, 1H); MS (ES+) m/z 450 (M+H)+.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 2 h
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with DCM
  6. filtrationfiltered
  7. washwashed with water, brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-913a04f4e9d342d29174bb7c35bbe818
Source dataset
uspto-grants-2010_09
Patent number
US07795250B2

Reaction notes

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