Toluene → HCID 54197412, compound

HRID 1780426Notes

Reaction equation

HRID 1780426 reaction equation
[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:17])([C:7]3[CH:15]=[CH:14][C:13](Br)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:18].[S:19]([NH:35][C:36]1[CH:37]=[C:38](B(O)O)[CH:39]=[CH:40][CH:41]=1)([C:22]1[C:34]2[CH:33]=[CH:32][CH:31]=[C:27]([N:28]([CH3:30])[CH3:29])[C:26]=2[CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20].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.CO>[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:17])([C:7]3[CH:15]=[CH:14][C:13]([C:38]4[CH:39]=[CH:40][CH:41]=[C:36]([NH:35][S:19]([C:22]5[C:34]6[C:26](=[C:27]([N:28]([CH3:30])[CH3:29])[CH:31]=[CH:32][CH:33]=6)[CH:25]=[CH:24][CH:23]=5)(=[O:21])=[O:20])[CH:37]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:18]

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 150643N-Dansyl-3-aminobenzeneboronic acidHCID 15355317(4aR)-(10bR)-4,10b-dimethyl-8-bromo-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one

Product 1

HCID 54197412HCID 54197412, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-8-bromo-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (83 mg, 0.27 mmol), tetrakis(triphenylphosphine) palladium (0) (23 mg, 0.02 mmol), 3-dansylaminophenylboronic acid (99 mg, 0.27 mmol), 0.3 mL of 2M sodium carbonate solution, 0.5 mL of toluene, and 0.1 mL of methanol, 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 (75 mL) and washed with brine (2×25 mL). The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (ethyl acetate eluent), to give 94 mg (63%) of the title compound as a yellow solid. mp 130°-140° (decomp.) FDMS: m/e=553. α[D]589 =+3.01 (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 (2×25 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-9b8ab6467d954983a56bd6d02f9271d2
Source dataset
uspto-grants-1997_05
Patent number
US05629007

Reaction notes

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