Toluene → HCID 54033918, compound

HRID 1780428Notes

Reaction equation

HRID 1780428 reaction equation
Br[C:2]1[CH:17]=[CH:16][C:5]2[C@:6]3([CH3:15])[C@@H:11]([CH2:12][CH2:13][C:4]=2[CH:3]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]3.[N+:18]([C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)([O-:20])=[O:19].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>ClCCl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N+:18]([C:21]1[CH:26]=[C:25]([C:2]2[CH:17]=[CH:16][C:5]3[C@:6]4([CH3:15])[C@@H:11]([CH2:12][CH2:13][C:4]=3[CH:3]=2)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]4)[CH:24]=[CH:23][CH:22]=1)([O-:20])=[O:19]

Participants

7

Reactant 4

HCID 1140TolueneHCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 11119935HCID 11119935, compound

Product 1

HCID 54033918HCID 54033918, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-8-bromo-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (500 mg, 1.70 mmol), tetrakis(triphenylphosphine) palladium (0) (80 mg, 0.07 mmol), 3-nitrophenylboronic acid (426 mg, 2.55 mmol), 2.4 mL of 2M sodium carbonate and 4 mL of toluene, fitted with a reflux condenser, and the stirred mixture was heated at 80°, under nitrogen, for 24 h. The mixture was cooled, diluted with dichloromethane (200 mL) and washed with brine (2×50 mL). The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (ethyl acetate eluent) to give 456 mg (80%) of the title compound as a white solid. mp 223°-225°. FDMS: m/e=336. α[D]589 =+45.63 (c=1.03, methanol).

Workup

  1. customfitted with a reflux condenser
  2. temperaturethe stirred mixture was heated at 80°, under nitrogen, for 24 h
  3. temperatureThe mixture was cooled
  4. washwashed with brine (2×50 mL)
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (ethyl acetate eluent)

Sources & evidence

ORD record
ord-746959c91f4f4882b785738680b7b661
Source dataset
uspto-grants-1997_05
Patent number
US05629007

Reaction notes

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