Potassium Carbonate → HCID 68161500, compound

HRID 2041776Notes

Reaction equation

OB(O)[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[C:13]([N:16]1[C:25]2[C:20](=[CH:21][C:22](Br)=[CH:23][CH:24]=2)[C@H:19]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:18][C@@H:17]1[CH2:34][CH2:35][CH3:36])(=[O:15])[CH3:14].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:13]([N:16]1[C:25]2[C:20](=[CH:21][C:22]([C:3]3[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=3)=[CH:23][CH:24]=2)[C@H:19]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:18][C@@H:17]1[CH2:34][CH2:35][CH3:36])(=[O:15])[CH3:14]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 4-(dihydroxyboranyl)benzoic acid (25.7 mg, 0.155 mmol), (cis)-1-acetyl-6-bromo-N-phenyl-2-propyl-1,2,3,4-tetrahydro-4-quinolinamine (for a preparation see intermediate 86) (40 mg, 0.103 mmol), tetrakis(triphenylphosphine)palladium(0) (11.93 mg, 10.33 μmol) and potassium carbonate (42.8 mg, 0.310 mmol) in 1,4-dioxane (1 mL) and water (0.5 mL) was stirred at 130° C. for 15 min under microwave irradiation then cooled to room temperature and concentrated in vacuo. Purification of the residue by MDAP (modifier:formic acid) gave 4-[(cis)-1-acetyl-4-(phenylamino)-2-propyl-1,2,3,4-tetrahydro-6-quinolinyl]benzoic acid (19 mg, 0.044 mmol, 43%).

Workup

temperaturethen cooled to room temperature
concentrationconcentrated in vacuo
customPurification of the residue by MDAP (modifier:formic acid)

Sources & evidence

ORD record: ord-5031ca9220b44acb9eeb7c380ec6e446
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580957B2

Reaction notes

Loading…