Triethylamine → HCID 24774131, compound

HRID 1047076Notes

Reaction equation

HRID 1047076 reaction equation
CCN(CC)CC.Br[CH2:9][CH2:10][CH2:11][CH2:12][C:13](Cl)=[O:14].[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([B:23]2[O:31][C:28]([CH3:30])([CH3:29])[C:25]([CH3:27])([CH3:26])[O:24]2)=[CH:19][CH:18]=1.[H-].[Na+]>C(Cl)Cl.CN(C=O)C>[CH3:29][C:28]1([CH3:30])[C:25]([CH3:26])([CH3:27])[O:24][B:23]([C:20]2[CH:21]=[CH:22][C:17]([N:16]3[CH2:9][CH2:10][CH2:11][CH2:12][C:13]3=[O:14])=[CH:18][CH:19]=2)[O:31]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24758Sodium hydrideHCID 5211735-Bromovaleryl chlorideHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 24774131HCID 24774131, compoundYield 36.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Et3N (239 μL, 1.71 mmol) and 5-bromovaleroyl chloride (166 μL, 1.26 mmol) were added to a solution of 4-aminophenylboronic acid pinacol ester (250 mg, 1.14 mmol) in DCM (5 mL) at 0° C. After stirring the mixture for 18.5 hours at room temperature, the mixture was concentrated. The residue was diluted with EtOAc and washed with sat. NaHCO3 and brine. The organic layer was dried over anhydrous Na2SO4, and concentrated. The residue was diluted with DMF (5 mL) and NaH (55% in liquid paraffin, 62.2 mg, 1.43 mmol) at 0° C. After stirring the mixture for 21 hours at room temperature, the mixture was concentrated. The residue was diluted with 10% aqueous citric acid and extracted with DCM (3×). The combined organic layers were dried over anhydrous Na2SO4, and concentrated. The residue was purified by PTLC (EtOAc/hexane=1:1) to afford desired product (124 mg, 36.1%) as white solid. 1HNMR (CDCl3) 400 MHz δ: 7.86-7.81 (m, 2H), 7.30-7.24 (m, 2H), 3.70-3.60 (m, 2H), 2.61-2.51 (m, 2H), 2.00-1.87 (m, 4H), 1.33 (s, 12H).

Workup

  1. concentrationthe mixture was concentrated
  2. additionThe residue was diluted with EtOAc
  3. washwashed with sat. NaHCO3 and brine
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. stirringAfter stirring the mixture for 21 hours at room temperature
  7. concentrationthe mixture was concentrated
  8. additionThe residue was diluted with 10% aqueous citric acid
  9. extractionextracted with DCM (3×)
  10. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  11. concentrationconcentrated
  12. customThe residue was purified by PTLC (EtOAc/hexane=1:1)

Sources & evidence

ORD record
ord-cea81fb7e90e4a3cbff89cca0e79af21
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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