Triethylamine → HCID 59783741, compound

HRID 1946640Notes

Reaction equation

HRID 1946640 reaction equation
[CH:1]1[C:6]2[C:7](=[O:16])[NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH2:24]([O:26][C:27]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)=[O:28])[CH3:25]>C1COCC1.ClCCl.C(OCC)(=O)C.C(O[Cu]OC(=O)C)(=O)C>[O:16]=[C:7]1[C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[O:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]1[C:32]1[CH:33]=[CH:34][C:29]([C:27]([O:26][CH2:24][CH3:25])=[O:28])=[CH:30][CH:31]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 72374O-(o-Aminophenoxy)benzoic acid lactamHCID 27343504-Ethoxycarbonylphenylboronic acid

Product 1

HCID 59783741HCID 59783741, compoundYield 23.4%

Reagents, catalysts & solvents 4

HCID 178476681HCID 178476681, compoundCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of dibenzo[b,f][1,4]oxazepin-11(10H)-one (0.623 g, 2.95 mmol) in THF (10.0 mL), dichloromethane (10.0 mL) and triethylamine (2.0 mL, 14.7 mmol) was added diacetoxycopper (0.587 g, 3.25 mmol) followed by 4-(ethoxycarbonyl)phenylboronic acid (1.15 g, 5.91 mmol). The reaction mixture was stirred at room temperature for 5 days. It was diluted with ethyl acetate and this organic layer was washed with 10% HCl (2 times), water and brine, dried over sodium sulfate, filtered and evaporated. The crude was purified by flash chromatography (a 1st one with 20% ethyl acetate in hexanes and second one with 0.5% methanol in dichloromethane) to afford title compound 465 (248 mg, 23%) as a white solid. MS (m/z): 360.3 (M+H).

Workup

  1. washthis organic layer was washed with 10% HCl (2 times), water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude was purified by flash chromatography (a 1st one with 20% ethyl acetate in hexanes and second one with 0.5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-0d1e346891dd4fa381ca6fd7abae9eab
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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