Potassium Phosphate, Tribasic → HCID 66835778, compound

HRID 2275277Notes

Reaction equation

HRID 2275277 reaction equation
Br[C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7](=[O:30])[C:8]4[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@H:23]5[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24]5)=[CH:17][C:9]=4[C:10]([CH3:16])([CH3:15])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.[S:31]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CC(N(C)C)=O.O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:29][C:25]1([CH3:28])[O:24][C@@H:23]([CH2:22][O:21][C:18]2[CH:19]=[CH:20][C:8]3[C:7](=[O:30])[C:6]4[C:5]5[C:13](=[CH:14][C:2]([C:33]6[CH:34]=[CH:35][S:31][CH:32]=6)=[CH:3][CH:4]=5)[NH:12][C:11]=4[C:10]([CH3:15])([CH3:16])[C:9]=3[CH:17]=2)[CH2:27][O:26]1

Participants

8

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 581760Thiophene-3-boronic acidHCID 668346753-bromo-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one

Product 1

HCID 66835778HCID 66835778, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

3-Bromo-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (20.0 mg, 0.043 mmol), thiophene-3-boronic acid (10.9 mg, 0.085 mmol), K3PO4 (40 mg) and Pd (PPh3)4 (9.9 mg, 0.0086 mmol) were dissolved in DMA (0.8 ml) and water (0.2 ml), and stirred at 140° C. for 10 min under microwave irradiation. The reaction solution was diluted with ethyl acetate and washed with saturated brine. The organic layer was concentrated under reduced pressure, and the resulting residues were purified by column chromatography (hexane/ethyl acetate) to obtain 8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-3-thiphen-3-yl-5,6-dihydro-benzo[b]carbazol-11-one.

Workup

  1. washwashed with saturated brine
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe resulting residues were purified by column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bb377cf008834a0bb8970ac3288e1624
Source dataset
uspto-grants-2015_09
Patent number
US09126931B2

Reaction notes

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