Acetonitrile → HCID 50943694, compound

HRID 2364631Notes

Reaction equation

HRID 2364631 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:23](Br)=[CH:22][C:20]=2[N:21]=1.[C:36](=[O:39])([O-])[O-:37].[K+].[K+].[C:42](#N)[CH3:43]>CCOC(C)=O.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]([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:23]([C:8]3[CH:7]=[CH:6][C:5]([CH:3]4[CH2:43][CH2:42][O:37][C:36]4=[O:39])=[CH:10][CH:9]=3)=[CH:22][C:20]=2[N:21]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 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 50943694HCID 50943694, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

(1E,4E)-2-Amino-8-(4-(2-oxotetrahydrofuran-3-yl)phenyl)-N,N-dipropyl-3H-benzo[b]azepine-4-carboxamide (9%) was prepared as follows, substituting 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)dihydrofuran-2(3H)-one 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, CDCl3) δ 7.64-7.68 (m, 2H), 7.51-7.54 (m, 1H), 7.32-7.39 (m, 4H), 6.84 (s, 1H), 4.48-4.55 (m, 1H), 4.33-4.42 (m, 1H), 3.83-3.90 (m, 1H), 3.41-3.50 (m, 4H), 2.89 (s, 2H), 2.70-2.81 (m, 1H), 2.44-2.56 (m, 1H), 1.59-1.72 (m, 4H), 0.88-0.98 (m, 6H); m/z (APCI-pos) M+1=446.2.

Workup

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

Sources & evidence

ORD record
ord-bc3f81f4d8784441a57338f6b5121219
Source dataset
uspto-grants-2014_04
Patent number
US08691809B2

Reaction notes

Loading…