Sodium Carbonate → HCID 4135989, compound

HRID 240115Notes

Reaction equation

HRID 240115 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6](B(O)O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:14]3[CH:15]=[C:16]([NH2:17])[CH:18]=[CH:19][CH:20]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 115623-BromoanilineHCID 27343615-Indolylboronic acid

Product 1

HCID 4135989HCID 4135989, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Indole-5-boronic acid (0.111 g, 0.693 mmol) and 3-bromoaniline (0.05 mL, 0.462 mmol) were combined in DME (2 mL) in a flame-dried, round-bottom flask. Na2CO3 (2M, 0.485 mL, 0.970 mmol) and Pd(PPh3)4 (0.017 g, 0.014 mmol) were added to the stirred solution. The reaction was refluxed overnight under argon flow, and subsequently cooled to room temperature. The solvent was removed under vacuum and the resulting residue was resuspended in CH2Cl2. The organic phase was dried over MgSO4 and concentrated under vacuum. The crude product was purified by silica column chromatography (50-100% EtOAc/hexanes). The purification was monitored by TLC. The solvent was removed under vacuum from fractions containing product, resulting in 0.049 g in 50% yield.

Workup

  1. temperatureThe reaction was refluxed overnight under argon flow
  2. customThe solvent was removed under vacuum
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe crude product was purified by silica column chromatography (50-100% EtOAc/hexanes)
  6. customThe purification
  7. customThe solvent was removed under vacuum from fractions
  8. additioncontaining product
  9. customresulting in 0.049 g in 50% yield

Sources & evidence

ORD record
ord-db0e3fd74f654519a439e10f38bc9f49
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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