Potassium Carbonate → HCID 59332628, compound

HRID 656158Notes

Reaction equation

HRID 656158 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:14][CH:15]1[CH2:20][CH2:19][S:18](=[O:22])(=[O:21])[CH2:17][CH2:16]1.[O:23]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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:21]=[S:18]1(=[O:22])[CH2:19][CH2:20][CH:15]([CH2:14][C:5]2[C:4]3[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=[C:2]([C:25]4[CH:26]=[CH:27][O:23][CH:24]=4)[CH:3]=3)[NH:7][CH:6]=2)[CH2:16][CH2:17]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2734358Furan-3-boronic acidHCID 59332646HCID 59332646, compound

Product 1

HCID 59332628HCID 59332628, compoundYield 49.6%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

5-bromo-3-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methyl]-1H-indole-7-carboxamide (30 mg, 0.078 mmol), 3-furanylboronic acid (24.05 mg, 0.215 mmol, 2.76 eq), potassium carbonate (64.6 mg, 6 eq), PdCl2(dppf) (4.56 mg, 0.006 mmol, 0.08 eq), were dissolved in a mixture of 1,4-dioxane (2 mL) and water (1 mL) in a 2-5 mL biotage microwave reaction tube. The mixture was heated in a Biotage microwave at high absorption for 10 minutes at 120° C. The reaction mixture was filtered through a polypropylene cartridge (10 mL tube) on a Bohdan Miniblock in a reaction tube and was then concentrated and purified by Gilson HPLC with a water-acetonitrile with 0.1% TFA buffer. The desired product fractions were combined and concentrated in an EZ2 Genevac evaporator, giving 14.4 mg (44.7%) of the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through a polypropylene cartridge (10 mL tube) on a Bohdan Miniblock in a reaction tube
  2. concentrationwas then concentrated
  3. custompurified by Gilson HPLC with a water-acetonitrile with 0.1% TFA buffer
  4. concentrationconcentrated in an EZ2 Genevac evaporator

Sources & evidence

ORD record
ord-7cec584be6c6403f8d3bc0511b8bb42e
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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