Potassium Carbonate → HCID 68844189, compound

HRID 1784859Notes

Reaction equation

HRID 1784859 reaction equation
[CH3:1][O:2][C:3](=[O:40])[NH:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][N:15]3[Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:8]=[C:7]([C:30]([C:32]2[CH:37]=[C:36]([CH3:38])[N:35]=[C:34](Cl)[CH:33]=2)=[O:31])[CH:6]=1.[C:41](=O)([O-])[O-].[K+].[K+].CB(O)O>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:40])[NH:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][N:15]3[Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:8]=[C:7]([C:30]([C:32]2[CH:37]=[C:36]([CH3:38])[N:35]=[C:34]([CH3:41])[CH:33]=2)=[O:31])[CH:6]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 50994510HCID 50994510, compound

Product 1

HCID 68844189HCID 68844189, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To 0.100 g (0.174 mmol) [3-(2-chloro-6-methyl-pyridine-4-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-carbamic acid methyl ester in 2.0 mL of anhydrous dioxane in a pressure tube was added 0.034 g (0.24 mmol) potassium carbonate and 0.015 g (0.24 mmol) methylboronic acid. The reaction mixture was degassed with argon and then 0.006 g (0.005 mmol) Pd(PPh3)4 was added. The reaction mixture was capped and heated at 110° C. for 24 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate phase was washed with brine and dried over anhydrous sodium sulfate. The solution was filtered and concentrated. The crude product was chromatographed on silica gel using 10:1 methylene chloride:methanol to give 0.060 g of [3-(2,6-dimethyl-pyridine-4-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-carbamic acid methyl ester. The protecting group was removed as described in Example 75 to give [3-(2,6-dimethyl-pyridine-4-carbonyl)-5-(1H-indol-4-yl)-phenyl]-carbamic acid methyl ester. 1H NMR (400 MHz, CDCl3): δ 8.50 (s, 1H), 8.12 (s, 1H), 7.79-7.75 (m, 2H), 7.40 (d, J=8.2 Hz, 1H), 7.29 (s, 2H), 7.27-7.22 (m, 2H), 7.17 (dd, J=7.3, 0.9 Hz, 1H), 7.05 (s, 1H), 6.72 (s, 1H), 3.79 (s, 3H), 2.60 (s, 6H).

Workup

  1. customThe reaction mixture was degassed with argon
  2. customThe reaction mixture was capped
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate phase was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe solution was filtered
  7. concentrationconcentrated
  8. customThe crude product was chromatographed on silica gel using 10:1 methylene chloride

Sources & evidence

ORD record
ord-c068807f0c4a46f494b4226691e4f68e
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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