Potassium Carbonate → HCID 90120215, compound

HRID 2202552Notes

Reaction equation

HRID 2202552 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:25]1[NH:26][C:27](I)=[C:28](I)[N:29]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32][O:33][C:34]1[CH:35]=[C:36]2[C:41](=[CH:42][CH:43]=1)[CH:40]=[C:39](B(O)O)[CH:38]=[CH:37]2.C([O-])([O-])=O.[K+].[K+].COCCOC.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]>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:25]1[NH:26][C:27]([C:39]2[CH:38]=[CH:37][C:36]3[C:41](=[CH:42][CH:43]=[C:34]([O:33][CH3:32])[CH:35]=3)[CH:40]=2)=[CH:28][N:29]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 46416926-Methoxy-2-naphthaleneboronic acidHCID 18180031Water 1,2-dimethoxyethaneHCID 90120330HCID 90120330, compound

Product 1

HCID 90120215HCID 90120215, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A degassed microwave vial was charged with D4, (6-methoxy-2-naphthyl)boronic acid (2 eq.), PdCl2(dppf)2 (0.2 eq.) and K2CO3 (3 eq.). A degassed solution of DME/H2O (1:1, 0.05 M) was added and the suspension was degassed for further 10 minutes and then heated at 110° C. for 30 min. After cooling, reaction mixture was diluted with EtOAc and filtered through a pad of Solka-Floc®. The filtrate was washed with sat. aq. NaHCO3 sol., brine, dried over Na2SO4, filtered and concentrated to give a dark red residue. The resulting crude was purified by column chromatography (eluent: petroleum ether/EtOAc from 95:5 to 1:1) to give the title compound as a pale yellow solid. MS (ES+) C33H39N3O5: 558 (M+H)+.

Workup

  1. customthe suspension was degassed for further 10 minutes
  2. temperatureAfter cooling
  3. customreaction mixture
  4. filtrationfiltered through a pad of Solka-Floc®
  5. washThe filtrate was washed with sat. aq. NaHCO3 sol., brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a dark red residue
  10. customThe resulting crude was purified by column chromatography (eluent: petroleum ether/EtOAc from 95:5 to 1:1)

Sources & evidence

ORD record
ord-6ad31ac997184afcb9ce9044f735faf4
Source dataset
uspto-grants-2016_06
Patent number
US09365541B2

Reaction notes

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