Potassium Carbonate → HCID 86718778, compound

HRID 929598Notes

Reaction equation

Br[C:2]1[C:11]2[O:10][CH2:9][N:8]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][C:28]=1[Cl:29]>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>[C:12]([N:8]1[CH2:7][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([C:26]3[CH:25]=[CH:24][C:23]([Cl:22])=[C:28]([Cl:29])[CH:27]=3)[C:11]=2[O:10][CH2:9]1)([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 58.5 °C

Procedure

A mixture of 8-bromo-3-(tert-butyl)-3,4-dihydro-2H-benzo[e][1,3]oxazine (0.46 g, 1.71 mmol), potassium carbonate (0.945 g, 4.0 equiv), 3,4-dichlorophenylboronic acid (0.489 g, 1.5 equiv), and tetrakis(triphenylphosphine)Pd (0) (63 mg, 3.2 mol %) was heated at 53-64° C. for 3 hours, then at 80-87° C. for 2.5 hours. To the mixture was added additional 3,4-dichlorophenylboronic acid (0.2 g) and the resulting mixture was heated at 80-87° C. overnight. Upon cooling to room temperature, the reaction mixture was concentrated. The crude product was purified by column chromatography to give 3-(tert-butyl)-8-(3,4-dichlorophenyl)-3,4-dihydro-2H-benzo[e][1,3]oxazine (0.313 g) as yellow oil.

Workup

temperaturethe resulting mixture was heated at 80-87° C. overnight
temperatureUpon cooling to room temperature
concentrationthe reaction mixture was concentrated
customThe crude product was purified by column chromatography

Sources & evidence

ORD record: ord-2e9585fe5f9b46c2b17c02c8a48e1e3b
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296696B2

Reaction notes

Loading…