Triethylamine → HCID 67503029, compound

HRID 1047079Notes

Reaction equation

HRID 1047079 reaction equation
CCN(CC)CC.[CH:8]1([C:11](Cl)=[O:12])[CH2:10][CH2:9]1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([B:21]2[O:29][C:26]([CH3:28])([CH3:27])[C:23]([CH3:25])([CH3:24])[O:22]2)=[CH:17][CH:16]=1>C(Cl)Cl>[CH3:27][C:26]1([CH3:28])[C:23]([CH3:24])([CH3:25])[O:22][B:21]([C:18]2[CH:19]=[CH:20][C:15]([NH:14][C:11]([CH:8]3[CH2:10][CH2:9]3)=[O:12])=[CH:16][CH:17]=2)[O:29]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 67503029HCID 67503029, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Et3N (239 μL, 1.71 mmol) and cyclopropanecarbonyl chloride (114 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 4 hours at room temperature, the mixture was concentrated. The residue was diluted with EtOAc and washed with 10% aqueous citric acid, sat. NaHCO3 and brine. The organic layer was dried over anhydrous Na2SO4, and concentrated. The residue was purified by silica gel column chromatography (EtOAc/hexane=9:1→4:1) to afford desired product (291 mg, 88.9%) as white solid. 1HNMR (CDCl3) 400 MHz δ: 7.82-7.70 (m, 2H), 7.59-7.47 (m, 2H), 7.43 (br s, 1H), 1.54-1.44 (m, 1H), 1.33 (s, 12H), 1.09 (dt, J=7.4, 4.2 Hz, 2H), 0.85 (td, J=7.4, 4.2 Hz, 2H).

Workup

  1. concentrationthe mixture was concentrated
  2. additionThe residue was diluted with EtOAc
  3. washwashed with 10% aqueous citric acid, sat. NaHCO3 and brine
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane=9:1→4:1)

Sources & evidence

ORD record
ord-583388826f1347e9a6bf2dfd5dc0f27e
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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