Sodium Carbonate → HCID 57722842, compound

HRID 222297Notes

Reaction equation

HRID 222297 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]2[CH:25]=[CH:24][C:18]3=[N:19][CH:20]=[C:21](Cl)[CH:22]=[C:17]3[C:16](=[O:26])[C:15]=2[CH:27]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:28][N:29]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[N:30]1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]2[CH:25]=[CH:24][C:18]3=[N:19][CH:20]=[C:21]([C:32]4[CH:31]=[N:30][N:29]([CH3:28])[CH:33]=4)[CH:22]=[C:17]3[C:16](=[O:26])[C:15]=2[CH:27]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 57722763HCID 57722763, compound

Product 1

HCID 57722842HCID 57722842, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

A test tube fitted with a teflon septum was charged with 7-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-chloro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (9 mg, 0.023 mmol), PdCl2(PPh3)2 (2 mg, 0.002 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (14 mg, 0.068 mmol), and sodium carbonate (7 mg, 0.068 mmol). The tube was evacuated and backfilled with argon three times. Fully degassed dioxane (0.5 mL) was added and the mixture was stirred at 100° C. overnight. The solution was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate, concentrated in vacuo, and purified via flash chromatography (silica, 20-100% ethyl acetate/hexanes) to afford the title compound. LRMS (APCI) calc'd for (C26H32N3O2Si) [M+H]+, 446.2; found 446.2.

Workup

  1. customThe tube was evacuated
  2. additionFully degassed dioxane (0.5 mL) was added
  3. additionThe solution was diluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified via flash chromatography (silica, 20-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-7d8bcf2060aa47939d0c18c3e4645c02
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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