Sodium Carbonate → HCID 86593171, compound

HRID 1266066Notes

Reaction equation

HRID 1266066 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9]3=[C:10]([C@H:12]4[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15][CH2:14][C@H:13]4[N:8]3[CH2:7][CH2:6][CH2:5]2)[CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:31][C:32]1[C:37]([Cl:38])=[CH:36][CH:35]=[CH:34][C:33]=1B(O)O.P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>COCCOC.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]>[Cl:31][C:32]1[C:37]([Cl:38])=[CH:36][CH:35]=[CH:34][C:33]=1[C:2]1[CH:3]=[C:4]2[C:9]3=[C:10]([C@H:12]4[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:15][CH2:14][C@H:13]4[N:8]3[CH2:7][CH2:6][CH2:5]2)[CH:11]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27346612,3-Dichlorobenzeneboronic acidHCID 10157379HCID 10157379, compound

Product 1

HCID 86593171HCID 86593171, compoundYield 125.9%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Tert-butyl (±)-cis-2-bromo-5,6,8,9,11,11a-hexahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline-10(7aH)-carboxylate (110 mg, 0.28 mmol) was dissolved in DME (4 mL). 2M aqueous sodium carbonate (0.75 ml) was added. 2,3-Dichlorophenylboronic acid (107 mg, 0.56 mmol) was added, followed by Pd2(dba)3 (14.5 mg, .014 mmol). P(Ph)3 (14.7 mg, 0.056 mmol) was added. The reaction flask was degassed and kept under a nitrogen atmosphere. The suspension was refluxed for 18 h cooled to rt. The reaction was concentrated in vacuo, after which water (10 mL) and EtOAc (10 mL) were added. The layers were separated and the aqueous phase was extracted with EtOAc (2×10 mL). The combined organic layers were washed with brine (2×10 mL), dried, and concentrated to afford a crude brown amorphous solid (162 mg). The residue was purified by column chromatography (20-0% hexane/CH2Cl2) to afford the title compound (96.8 mg, 75%) as a white amorphous solid. 1H NMR (CDCl3, 300 MHz) δ7.61-7.94 (m, 1H), 7.20 (s, 1 H), 7.18 (d, 1H, 3.3 Hz), 7.00 (s, 1H), 6.93 (s, 1H), 3.70-3.74 (m, 1H), 3.45-60 (m, 1H), 3.15-3.35 (m, 4H), 2.65-2.80 (m, 4H), 2.10-2.20 (m, 2H), 1.80-2.00 (m, 2H), 1.46 (s, 9H) ppm.

Workup

  1. customThe reaction flask was degassed
  2. temperatureThe suspension was refluxed for 18 h
  3. concentrationThe reaction was concentrated in vacuo
  4. additionafter which water (10 mL) and EtOAc (10 mL) were added
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with EtOAc (2×10 mL)
  7. washThe combined organic layers were washed with brine (2×10 mL)
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9d4dac54f970464dbecf2dbc7edd3ec9
Source dataset
uspto-grants-2003_04
Patent number
US06548493B1

Reaction notes

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