Sodium Carbonate → HCID 50992382, compound

HRID 1499024Notes

Reaction equation

HRID 1499024 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:5]2[O:10][C:9]3[N:11]=[CH:12][C:13]([CH2:15][N:16]([CH3:18])[CH3:17])=[CH:14][C:8]=3[C:6]=2[N:7]=1.[NH:25]1[C:33]2[CH:32]=[CH:31][CH:30]=[C:29](B(O)O)[C:28]=2[CH:27]=[CH:26]1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>CCOC(C)=O.[Cl-].[Na+].O.O>[NH:25]1[C:33]2[C:28](=[C:29]([C:2]3[N:3]=[C:4]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[C:5]4[O:10][C:9]5[N:11]=[CH:12][C:13]([CH2:15][N:16]([CH3:18])[CH3:17])=[CH:14][C:8]=5[C:6]=4[N:7]=3)[CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27631731H-Indole-4-boronic acidHCID 87207588HCID 87207588, compound

Product 1

HCID 50992382HCID 50992382, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
88 °C

Procedure

To a sealed tube was added 9 (5 mg, 0.014 mmol), indole-4-boronic acid (5.8 mg, 0.036 mmol), dichloro-bis(triphenylphosphine)palladium (II) (2.0mg, 0.0029 mmol) and Na2CO3 (3.1 mg, 0.029 mmol) followed by dioxane (2 mL) and water (0.8 mL) under Ar(g). The lid was sealed and the tube was heated to 88° C. for 18 h whereupon it was cooled to rt and diluted with EtOAc (35 mL) and 50% saturated brine (5 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (2×10 mL). The combined organic layers were then dried (MgSO4) and concentrated in vacuo. Purification by flash column chromatography on silica (eluant 2-5% MeOH/CH2Cl2) furnished H (2 mg, 0.005 mmol, 32%) as an off-white solid.

Workup

  1. customThe lid was sealed
  2. temperaturewas cooled to rt
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with EtOAc (2×10 mL)
  5. dry with materialThe combined organic layers were then dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography on silica (eluant 2-5% MeOH/CH2Cl2)
  8. customfurnished H (2 mg, 0.005 mmol, 32%) as an off-white solid

Sources & evidence

ORD record
ord-a1e6ed6580f241d095054e8bc44c1d6e
Source dataset
uspto-grants-2015_12
Patent number
US09200007B2

Reaction notes

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