Triethylamine → HCID 136414047, compound

HRID 1403395Notes

Reaction equation

HRID 1403395 reaction equation
Br[C:2]1[C:11]([N:12]([CH3:16])[CH:13]([CH3:15])[CH3:14])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[O:18])[CH:8]=2)[N:3]=1.[OH:29][C:30]1[CH:37]=[CH:36][C:35](B2OC(C)(C)C(C)(C)O2)=[CH:34][C:31]=1[CH:32]=[O:33].CCN(CC)CC>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:32]([C:31]1[CH:34]=[C:35]([C:2]2[C:11]([N:12]([CH3:16])[CH:13]([CH3:15])[CH3:14])=[N:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:17]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=4)=[O:18])[CH:8]=3)[N:3]=2)[CH:36]=[CH:37][C:30]=1[OH:29])=[O:33]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 116588402-Hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzaldehydeHCID 86670561HCID 86670561, compound

Product 1

HCID 136414047HCID 136414047, compoundYield 43.5%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (4-methoxyphenyl)methyl 2-bromo-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate (400 mg, 0.90 mmol) in 1,2-dimethoxyethane (10 mL) was added 2-hydroxy-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (444 mg, 2.26 mmol), Et3N (273 mg, 2.7 mmol), Pd(dppf)Cl2 (58 mg, 0.08 mmol) and water (5 drops). The resulting solution was stirred for 1 h at 90° C. and maintained under an inert atmosphere of nitrogen in an oil bath. The reaction mixture was concentrated in vacuo to give the residue, which was purified by silica gel column chromatography eluting with 1% to 5% ethyl acetate in petroleum to afford (4-methoxyphenyl)methyl 2-(3-formyl-4-hydroxyphenyl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate as a yellow solid (190 mg, 43%).

Workup

  1. temperaturemaintained under an inert atmosphere of nitrogen in an oil bath
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto give the residue, which
  4. customwas purified by silica gel column chromatography
  5. washeluting with 1% to 5% ethyl acetate in petroleum

Sources & evidence

ORD record
ord-b4752115ddf6436dbcca3483969b1c78
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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