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Potassium Carbonate → ethyl 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate

HRID 572351
Notes
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Reaction equation

HRID 572351 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[C:14]([N:17]1[C:26]2[C:21](=[CH:22][C:23](B3OC(C)(C)C(C)(C)O3)=[CH:24][CH:25]=2)[C@H:20]([NH:36][C:37](=[O:42])[O:38][CH:39]([CH3:41])[CH3:40])[CH2:19][C@@H:18]1[CH3:43])(=[O:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[C:14]([N:17]1[C:26]2[C:21](=[CH:22][C:23]([C:2]3[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=3)=[CH:24][CH:25]=2)[C@H:20]([NH:36][C:37]([O:38][CH:39]([CH3:41])[CH3:40])=[O:42])[CH2:19][C@@H:18]1[CH3:43])(=[O:16])[CH3:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 7020609Ethyl 2-(4-bromophenyl)acetateHCID 681853941-Methylethyl [(cis)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate

Product 1

HCID 68185396ethyl 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate
Yield 59.7%

Reagents, catalysts & solvents 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a flask was charged with ethyl (4-bromophenyl)acetate (0.174 mL, 1.000 mmol), 1-methylethyl [(2S,4R)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (416 mg, 1 mmol), potassium carbonate (415 mg, 3.00 mmol) and PdCl2(dppf) (73.2 mg, 0.100 mmol) was added 1,4-dioxane (6 mL) and water (2.0 mL) and the flask flushed with nitrogen. The resulting mixture was stirred under microwave irradiation at 120° C. for 30 min then cooled to room temperature. The bulk of dioxane was removed in vacuo and the residue partitioned between EtOAc and water. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by chromatography [(25 g column, MeOH/DCM)] to give ethyl 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate (270 mg, 59.7% yield). This compound was used in the next step without further purification. LCMS (HpH, 2 min), Rt=1.16, MH+=453.

Workup

  1. customthe flask flushed with nitrogen
  2. temperaturethen cooled to room temperature
  3. customThe bulk of dioxane was removed in vacuo
  4. customthe residue partitioned between EtOAc and water
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with EtOAc
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by chromatography [(25 g column, MeOH/DCM)]

Sources & evidence

ORD record
ord-077f8f5ddad449b6b43ce63ad8a360ce
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09029395B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes