Sodium Carbonate → HCID 45376496, compound

HRID 2195742Notes

Reaction equation

HRID 2195742 reaction equation
[CH:1]1([C@H:7]([NH:12][C:13]([C:15]2[O:16][C:17](Br)=[CH:18][CH:19]=2)=[O:14])[C:8](=[O:11])[NH:9][CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27](B(O)O)[CH:28]=2)[CH:23]=[CH:22]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[CH:1]1([C@H:7]([NH:12][C:13]([C:15]2[O:16][C:17]([C:27]3[CH:28]=[C:29]4[C:24]([CH:23]=[CH:22][NH:21]4)=[CH:25][CH:26]=3)=[CH:18][CH:19]=2)=[O:14])[C:8](=[O:11])[NH:9][CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27632051H-Indol-6-ylboronic acidHCID 58505545HCID 58505545, compound

Product 1

HCID 45376496HCID 45376496, compound

Reagents, catalysts & solvents 2

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a pressure vial 5-Bromo-furan-2-carboxylic acid ((S)-cyclohexyl-methylcarbamoyl-methyl)-amide (190 mg, 0.55 mmol), indole-6-boronic acid (106 mg, 0.66 mmol), and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (39 mg, 0.05 mmol) are dissolved in DMF (3 mL). A 2M sodium carbonate solution (3.0 mL) is added and the resulting solution is degassed with Argon during 5 min. The vessel was heated at 100° C. for 20 min in the Microwave. Upon cooling the resulting mixture is diluted with EtOAc/H2O and the aqueous phase is extracted with EtOAc. The combined organic extracts are washed with brine, dried over MgSO4, and the solvent is evaporated. The residue is purified using reversed phase (HPLC). 137 mg, 65% LC/MS ESI m/z (M+H)+=380.5.

Workup

  1. customthe resulting solution is degassed with Argon during 5 min
  2. temperatureUpon cooling the resulting mixture
  3. additionis diluted with EtOAc/H2O
  4. extractionthe aqueous phase is extracted with EtOAc
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried over MgSO4
  7. customthe solvent is evaporated
  8. customThe residue is purified

Sources & evidence

ORD record
ord-33d0897c031a4b728f48251914516223
Source dataset
uspto-grants-2012_12
Patent number
US08338367B2

Reaction notes

Loading…