Cesium carbonate → (4-{Acetyl-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-amino)-phenoxy)-acetic acid methyl ester

HRID 1785924Notes

Reaction equation

HRID 1785924 reaction equation
[NH2:1][C@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[O:13])[C@@H:4]([CH3:22])[CH2:3]1.[CH3:23][O:24][C:25](=[O:35])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31](Br)=[CH:30][CH:29]=1.C1(P([CH:58]2[CH2:63]CCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.C(=O)([O-])[O-:65].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:23][O:24][C:25](=[O:35])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([N:1]([C:63](=[O:65])[CH3:58])[CH:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([C:12](=[O:13])[C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[CH:4]([CH3:22])[CH2:3]2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 700580Methyl 2-(4-bromophenoxy)acetateHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 68918635(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-amine

Product 1

HCID 68921236(4-{Acetyl-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-amino)-phenoxy)-acetic acid methyl esterYield 368.1%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

(2S,4R)-(4-Amino-2-methyl-3,4-dihydro-2H-quinolin-1-yl)-(4-methoxyphenyl)-methanone (100 mg, 0.34 mmol), methyl-2-(4-bromophenoxy)-acetate (91 mg, 0.37 mmol), Pd2(dba)3 (17 mg, 0.02 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (8 mg, 0.00002 mol) and cesium carbonate (0.163 g, 0.0005 mol) were taken in a round bottom flask which was then flushed with nitrogen gas through a rubber septum. Toluene (2 mL) was injected into the flask through the rubber septum and the reaction mixture was stirred at 100° C. for 24 h. After cooling to room temperature the reaction mixture was filtered through Celite® and evaporated to give the crude product (0.236 g). This crude product was purified by silica gel chromatography eluting with 100% hexanes to 50/50 hexanes/ethyl acetate gradient give the title compound (37 mg, 24%).

Workup

  1. customwhich was then flushed with nitrogen gas through a rubber septum
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. filtrationwas filtered through Celite®
  4. customevaporated
  5. customto give the crude product (0.236 g)
  6. customThis crude product was purified by silica gel chromatography
  7. washeluting with 100% hexanes to 50/50 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-e81126a2972b4b7b9b10dc3e1743a4d9
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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