Sodium Carbonate → HCID 44624489, compound

HRID 2390827Notes

Reaction equation

HRID 2390827 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:5]([O:21][CH3:22])=[C:6]([CH:20]=1)[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=1.[C:27]([O-:30])([O-])=O.[Na+].[Na+]>C(Cl)Cl.CO.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>[C:23]([C:4]1[C:5]([O:21][CH3:22])=[C:6]([CH:20]=[C:2]([C:9]2[C:27](=[O:30])[NH:15][CH:12]=[CH:11][CH:10]=2)[CH:3]=1)[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 67070011HCID 67070011, compound

Product 1

HCID 44624489HCID 44624489, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

step 5—A mixture of 120 (0.20 g, 0.46 mmol), 112 (0.095 g, 0.69 mmol), Pd(PPh3)4 (0.053 g, 0.046 mmol) and Na2CO3 (0.15 g, 1.4 mmol) in DCM/MeOH (3:1, 8 mL) was irradiated in microwave synthesizer at 115° C. for 35 min. The reaction mixture was filtered and the filtrate concentrated. The crude residue was purified by SiO2 chromatography eluting with DCM/MeOH/NH4OH and the recovered product triturated with ether to afford I-71 as a solid.

Workup

  1. customwas irradiated in microwave synthesizer at 115° C. for 35 min
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated
  4. customThe crude residue was purified by SiO2 chromatography
  5. washeluting with DCM/MeOH/NH4OH
  6. customthe recovered product triturated with ether
  7. customto afford I-71 as a solid

Sources & evidence

ORD record
ord-29d4b3ba610541c7bb37cdd7dd667e6f
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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