Ethyl Acetate → HCID 50943536, compound

HRID 2275715Notes

Reaction equation

HRID 2275715 reaction equation
CO[C:3]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)=O.[NH2:14][C:15]1[CH2:16][C:17]([C:27]([N:29]([CH2:33][CH2:34][CH3:35])[CH2:30][CH2:31][CH3:32])=[O:28])=[CH:18][C:19]2[CH:25]=[CH:24]C(Br)=[CH:22][C:20]=2[N:21]=1.C(=O)([O-])[O-:37].[K+].[K+].[CH3:42][CH2:43][O:44][C:45]([CH3:47])=[O:46]>C(#N)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>[NH2:14][C:15]1[CH2:16][C:17]([C:27](=[O:28])[N:29]([CH2:30][CH2:31][CH3:32])[CH2:33][CH2:34][CH3:35])=[CH:18][C:19]2[CH:25]=[CH:24][C:3]([C:5]3[CH:6]=[CH:7][C:8]([O:37][CH2:47][C:45]([O:44][CH2:43][CH3:42])=[O:46])=[CH:9][CH:10]=3)=[CH:22][C:20]=2[N:21]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acid2×HCID 66961446(1E,4E)-2-amino-8-bromo-N,N-dipropyl-3H-benzo[b]azepine-4-carboxamide

Product 1

HCID 50943536HCID 50943536, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 2-(4-((1E,4E)-2-amino-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-8-yl)phenoxy)acetate (21%) was prepared as follows, substituting ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)acetate for 4-(methoxycarbonyl)phenylboronic acid. (1E,4E)-2-amino-8-bromo-N,N-dipropyl-3H-benzo[b]azepine-4-carboxamide (75.0 mgs, 0.206 mmol), 4-(methoxycarbonyl)phenylboronic acid (55.6 mgs, 0.309 mmol, tetrakis(triphenylphosphine)palladium(0) (23.8 mgs, 0.021 mmol), 2M aqueous potassium carbonate (0.309 ml, 0.618 mmol) were combined in 2 mls of acetonitrile in a microwave reaction vial. This mixture was heated in a microwave to 100° C. for 30 minutes. The mixture was then diluted with EtOAc, washed twice with brine, dried over sodium sulfate, and concentrated under reduced pressure. Preparative thin layer chromatography (2×0.5 mm plates, 7% MeOH/DCM) was then used. 1H NMR (400 MHz, DMSO-d6) δ 7.58-7.63 (m, 2H), 7.33-7.37 (m, 1H), 7.19-7.26 (m, 2H), 6.98-7.03 (m, 2H), 6.75 (s, 1H), 4.82 (s, 2H), 4.15-4.22 (m, 2H), 3.25-334 (m, 4H), 2.76 (s, 2H), 1.50-1.61 (m, 4H), 1.19-1.26 (m, 3H), 0.73-0.90 (m, 6H); m/z (APCI-pos) M+1=464.3.

Workup

  1. washwashed twice with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-38960f44647f417bac32caab5d2ca5e7
Source dataset
uspto-grants-2015_09
Patent number
US09126940B2

Reaction notes

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