Lithium Hydroxide → HCID 16047780, compound

HRID 1690673Notes

Reaction equation

HRID 1690673 reaction equation
C[O:2][C:3]([C:5]1[C:23]([OH:24])=[CH:22][C:8]2[C:9]3[NH:10][C:11]4[C:16]([C:17]=3[CH2:18][CH2:19][C:7]=2[CH:6]=1)=[CH:15][C:14](Br)=[CH:13][C:12]=4[F:21])=[O:4].[CH2:25]([Sn](CCCC)(CCCC)CCCC)[CH:26]=[CH2:27].[F-].[Cs+].[OH-].[Li+]>C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[Pd]>[CH2:27]([C:14]1[CH:15]=[C:16]2[C:11](=[C:12]([F:21])[CH:13]=1)[NH:10][C:9]1[C:8]3[CH:22]=[C:23]([OH:24])[C:5]([C:3]([OH:2])=[O:4])=[CH:6][C:7]=3[CH2:19][CH2:18][C:17]2=1)[CH:26]=[CH2:25]

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 25953Cesium fluorideHCID 90628AllyltributylstannaneHCID 66904822HCID 66904822, compound

Product 1

HCID 16047780HCID 16047780, compound

Reagents, catalysts & solvents 1

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)Catalyst

Conditions

Temperature
100 °C

Procedure

To a mixture 8-bromo-10-fluoro-2-hydroxy-5,11-dihydro-6H-benzo[a]carbazole-3-carboxylic acid methyl ester (50 mg, 0.13 mmol) (example 19, step 1), allyltributyl tin (56 mg, 0.15 mmol), cesium fluoride (38 mg, 0.25 mmol) dioxane (2 mL, anhydrous), is added palladium bis(tri-tert-butylphosphine) (4 mg, 5% mmol) in a microwave reaction tube. The tube is sealed and the mixture is purged with N2 for 3 min and heated at 100° C. for 3 h. Then the mixture is cooled to room temperature and filtered. The filtrate is concentrated and re-dissolved in EtOH/H2O (1 mL/0.1 mL). To the mixture is added lithium hydroxide (30 mg, 1.3 mmol). The mixture is heated at 120° C. for 6 min under microwave irradiation. Then the crude mixture is filtered and applied to mass-trigger preparative HPLC for purification. The title compound is obtained as a yellow solid; ESMS m/z 338.1 (M+H+).

Workup

  1. customin a microwave reaction tube
  2. customThe tube is sealed
  3. customthe mixture is purged with N2 for 3 min
  4. temperatureThen the mixture is cooled to room temperature
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated
  7. dissolutionre-dissolved in EtOH/H2O (1 mL/0.1 mL)
  8. temperatureThe mixture is heated at 120° C. for 6 min under microwave irradiation
  9. filtrationThen the crude mixture is filtered
  10. customapplied to mass-trigger preparative HPLC for purification

Sources & evidence

ORD record
ord-e6355d596761473eb9f672459e1926ca
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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