Ethanol → HCID 67214482, compound

HRID 2421619Notes

Reaction equation

HRID 2421619 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:15]=[C:14](Br)[CH:13]=[C:6]([C:7]([NH:9][CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[Na+].[Na+].C(O)C>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.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:4]1[CH:15]=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=[C:6]([C:7](=[O:8])[NH:9][CH2:10][CH2:11][CH3:12])[CH:5]=1)=[O:17]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 672137155-Bromo-N-propyl-isophthalamic acid methyl ester

Product 1

HCID 67214482HCID 67214482, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Using Preparation Method 2, 68C (247 mg, 0.82 mmol) was reacted with phenyl boronic acid (109 mg, 0.9 mmol) in the presence of 5 mol % Pd(PPh3)4, 0.82 mL of 2N Na2CO3, 0.43 mL of Ethanol and 1.8 mL of toluene. The resulting reaction mixture was purified using SiO2 with CH2Cl2/AcOEt 98:2 to 90:10 to give a greenish oil (284 g, quant.). NMR 1H (ppm, CDCl3): 8.37 (t, J4=1.64 Hz, 1H), 8.27 (d. t., J3=6.03 Hz, J4=1.75 Hz, 1H), 7.63 (d, J3=6.97 Hz, 1H), 7.49-7.36 (m, 5H), 6.27 (br. s., 1H), 3.49-3.42 (m, 2H), 1.64 (sext., J3=7.25 Hz, 2H), 1.00 (t., J3=7.37 Hz, 3H).

Workup

  1. customThe resulting reaction mixture
  2. customwas purified
  3. customto give a greenish oil (284 g, quant.)

Sources & evidence

ORD record
ord-dc996464303343b387f5f3c7296d71a6
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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