Sodium Carbonate → HCID 67378682, compound

HRID 1517537Notes

Reaction equation

HRID 1517537 reaction equation
[C:1]([C:5]1[C:16]([O:17][CH3:18])=[CH:15][C:8]([CH2:9][NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:28]([O:35][C:36]1[C:41](Br)=[CH:40][CH:39]=[C:38]([CH3:43])[N:37]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([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>[CH2:28]([O:35][C:36]1[C:41]([C:7]2[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:16]([O:17][CH3:18])=[CH:15][C:8]=2[CH2:9][NH:10][S:11]([CH3:14])(=[O:12])=[O:13])=[CH:40][CH:39]=[C:38]([CH3:43])[N:37]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 670700372-(Benzyloxy)-3-bromo-6-methylpyridineHCID 67379155HCID 67379155, compound

Product 1

HCID 67378682HCID 67378682, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

step 2—A sealed tube containing 72 (51 mg, 0.13 mmol), 2-benzyloxy-3-bromo-6-methyl-pyridine (51 mg, 0.19 mmol), Na2CO3 (40 mg, 0.38 mmol) and Pd(PPh3)4 (15 mg, 0.013 mmol) in a mixture of MeOH (3 mL) and DCM (1 mL) was irradiated in a microwave synthesizer at 125° C. for 30 min. The reaction mixture was diluted with DCM, filtered through a pad of CELITE, and the filtrate was concentrated. The crude residue was purified on a preparative SiO2 TLC plate developed with 5% MeOH/DCM to afford 17 mg (28%) of N-[2-(2-benzyloxy-6-methyl-pyridin-3-yl)-4-tert-butyl-5-methoxy-benzyl]-methanesulfonamide (74).

Workup

  1. customstep 2—A sealed tube
  2. customwas irradiated in a microwave synthesizer at 125° C. for 30 min
  3. filtrationfiltered through a pad of CELITE
  4. concentrationthe filtrate was concentrated
  5. customThe crude residue was purified on a preparative SiO2 TLC plate

Sources & evidence

ORD record
ord-a4a796d965a34b798623070312b9fdf0
Source dataset
uspto-grants-2012_07
Patent number
US08232271B2

Reaction notes

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