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Sodium Carbonate → HCID 54064643, compound

HRID 1780403
Notes
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Reaction equation

HRID 1780403 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].[CH:19]([C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][C:26]=1[OH:27])=[O:20].C(=O)([O-])[O-].[Na+].[Na+].B(O)O>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.[Pd].C1(C)C=CC=CC=1>[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:17])([C:7]3[CH:15]=[CH:14][C:13]([C:23]4[CH:24]=[CH:25][C:26]([OH:27])=[C:21]([CH:19]=[O:20])[CH:22]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 61668Boronic AcidHCID 15355317(4aR)-(10bR)-4,10b-dimethyl-8-bromo-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-oneHCID 221253053-Formyl-4-hydroxyphenylboronic acid

Product 1

HCID 54064643HCID 54064643, compoundYield 37.4%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalyst
HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst
HCID 1140TolueneSolvent
HCID 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 (200 mg, 0.65 mmol), tetrakis(triphenylphosphine) palladium (0) (23 mg, 0.02 mmol), 3-formyl-4-hydroxyphenylboronic acid (129 mg, 0.78 mmol), 0.65 mL of 2M sodium carbonate solution and 2 mL of toluene, fitted with a reflux condenser, and the stirred mixture was heated at 80°, under nitrogen, for 24 h. Additional palladium reagent and boronic acid was added, and the mixture was heated for an additional 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), followed by recrystallization from ethyl acetate, to give 85 mg (37%) of the title compound as a white solid. mp 184°-187° FDMS: m/e=349.

Workup

  1. customfitted with a reflux condenser
  2. temperaturethe stirred mixture was heated at 80°, under nitrogen, for 24 h
  3. temperaturethe mixture was heated for an additional 24 h
  4. temperatureThe mixture was cooled
  5. washwashed with brine (2×25 mL)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography (ethyl acetate eluent)
  9. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-ec9c35b0d9a44222b8de68d2c90cd55a
Source dataset
uspto-grants-1997_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05629007

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes