Sodium Carbonate → HCID 67070110, compound

HRID 2390848Notes

Reaction equation

HRID 2390848 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:5]([O:24][CH3:25])=[C:6]([CH2:8][C:9]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=2)([C:11]#[N:12])[CH3:10])[CH:7]=1.[C:30]([O-:33])([O-])=O.[Na+].[Na+]>CO.C(Cl)Cl.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:26]([C:4]1[C:5]([O:24][CH3:25])=[C:6]([CH2:8][C:9]([C:13]2[CH:14]=[CH:15][C:16]([NH:19][S:20]([CH3:23])(=[O:21])=[O:22])=[CH:17][CH:18]=2)([C:11]#[N:12])[CH3:10])[CH:7]=[C:2]([C:6]2[C:30](=[O:33])[NH:12][CH:11]=[CH:9][CH:8]=2)[CH:3]=1)([CH3:27])([CH3:28])[CH3:29]

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 67070089HCID 67070089, compound

Product 1

HCID 67070110HCID 67070110, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

step 5—A sealed tube containing 288 (69 mg, 0.144 mmol), 112 (30 mg, 0.216 mmol), Pd(PPh3)4 (16 mg, 0.014 mmol), Na2CO3 (41 mg, 0.387 mmol) in a mixture of MeOH (3 mL) and DCM (1 mL) was irradiated in a microwave reactor at 115° C. for 30 minutes. The reaction mixture was concentrated, diluted with EtOAc, washed with brine, and dried na2so4, filtered and concentrated. The crude product was purified on a SiO2 preparative TLC plate developed with 20% EtOAc/hexane to afford 33 mg (49%) of I-196 a white solid (49% yield).

Workup

  1. customstep 5—A sealed tube
  2. customwas irradiated in a microwave reactor at 115° C. for 30 minutes
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with EtOAc
  5. washwashed with brine
  6. customdried na2so4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified on a SiO2 preparative TLC plate

Sources & evidence

ORD record
ord-6a2bde17b3344d62a6b809194b91fd4d
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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