Potassium Carbonate → HCID 59332798, compound

HRID 387263Notes

Reaction equation

HRID 387263 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13]C)=[O:12])[CH:10]=1)[N:7](C(OC(C)(C)C)=O)[CH:6]=[C:5]2[CH:22]1[CH2:28][CH2:27][CH2:26][S:25](=[O:30])(=[O:29])[CH2:24][CH2:23]1.C([O-])([O-])=O.[K+].[K+].[C:37]1(B(O)O)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O1CCOCC1.O.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:30]=[S:25]1(=[O:29])[CH2:26][CH2:27][CH2:28][CH:22]([C:5]2[C:4]3[C:8](=[C:9]([C:11]([OH:13])=[O:12])[CH:10]=[C:2]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[CH:3]=3)[NH:7][CH:6]=2)[CH2:23][CH2:24]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 59332776HCID 59332776, compound

Product 1

HCID 59332798HCID 59332798, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
120 °C

Procedure

The intermediate 1-(1,1-dimethylethyl) 7-methyl 5-bromo-3-(1,1-dioxido-4-thiepanyl)-1H-indole-1,7-dicarboxylate (88 mg, 0.18 mmol), PdCl2(dppf) (13 mg, 0.109 mmol), K2CO3 (75 mg, 0.54 mmol), and PhB(OH)2 (33 mg, 0.27 mmol) were mixed together and the taken up in dioxane/H2O (3/1, 2 mL). The reaction was heated in a microwave oven at 120° C. for 10 minutes. The mixture was diluted with AcOEt, washed with 1N HCl, H2O and brine, dried over MgSO4, and concentrated. The residue was dissolved in MeOH (5 mL). 6N NaOH (1 mL) was added and the mixture was stirred at room temperature overnight. The reaction was diluted with AcOEt, washed with 1N HCl, H2O, dried over MgSO4, and then concentrated, giving the title compound. LC/MS: m/z 384.1 (M+H), Rt 1.87 min.

Workup

  1. washwashed with 1N HCl, H2O and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in MeOH (5 mL)
  5. addition6N NaOH (1 mL) was added
  6. additionThe reaction was diluted with AcOEt
  7. washwashed with 1N HCl, H2O
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a63cec13e18d4091b1af2ff15019c038
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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