Potassium Carbonate → HCID 86669450, compound

HRID 2041722Notes

Reaction equation

[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].[C:12]([N:15]1[C:24]2[C:19](=[CH:20][C:21](Br)=[CH:22][CH:23]=2)[C@H:18]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:17][C@@H:16]1[CH2:33][CH3:34])(=[O:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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>[C:12]([N:15]1[C:24]2[C:19](=[CH:20][C:21]([C:6]3[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=3)=[CH:22][CH:23]=2)[C@H:18]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:17][C@@H:16]1[CH2:33][CH3:34])(=[O:14])[CH3:13]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of (4-formylphenyl)boronic acid (31.7 mg, 0.212 mmol), (cis)-1-acetyl-6-bromo-2-ethyl-N-phenyl-1,2,3,4-tetrahydro-4-quinolinamine (for a preparation see intermediate 90) (79 mg, 0.212 mmol) and tetrakis(triphenylphosphine)palladium(0) (15 mg, 0.013 mmol) in 1,4-dioxane (1 mL) and water (0.5 mL) was treated with potassium carbonate (45 mg, 0.326 mmol) and the resulting mixture was stirred at 130° C. for 15 min under microwave irradiation then cooled to room temperature and concentrated in vacuovacuo. Purification of the residue by SP4 using a 25 G silica cartridge (gradient:0 to 100% AcOEt in Hexanes) gave 4-[(cis)-1-acetyl-2-ethyl-4-(phenylamino)-1,2,3,4-tetrahydro-6-quinolinyl]benzaldehyde (67.8 mg, 0.17 mmol, 80%) as a yellow oil.

Workup

temperaturethen cooled to room temperature
concentrationconcentrated in vacuovacuo
customPurification of the residue by SP4

Sources & evidence

ORD record: ord-ffdcec432cb34c2aa7d4ea4b324b6bdd
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580957B2

Reaction notes

Loading…