Sodium Carbonate → HCID 67375964, compound

HRID 1517543Notes

Reaction equation

HRID 1517543 reaction equation
Br[C:2]1[CH:19]=[C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:17]([O:24][CH3:25])=[CH:16][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([CH3:14])[C:6]1=[O:15].[CH2:26]([O:33][C:34]1[C:39](B(O)O)=[CH:38][CH:37]=[CH:36][N:35]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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>[CH2:26]([O:33][C:34]1[C:39]([C:2]2[CH:19]=[C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:17]([O:24][CH3:25])=[CH:16][C:3]=2[CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[N:7]([CH3:14])[C:6]2=[O:15])=[CH:38][CH:37]=[CH:36][N:35]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 44755161[2-(Benzyloxy)pyridin-3-yl]boronic acidHCID 67375845HCID 67375845, compound

Product 1

HCID 67375964HCID 67375964, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

step 2—A sealed tube containing 96 (100 mg, 0.25 mmol), 2-benzyloxy-pyridin-3-yl boronic acid (85 mg, 0.37 mmol), Na2CO3 (80 mg, 0.74 mmol) and Pd(PPh3)4 (29 mg, 0.025 mmol) in a mixture of MeOH (1.5 mL) and DCM (0.5 mL) was irradiated on a microwave synthesizer at 100° 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 30% EtOAc/hexanes to afford 99 mg of 1-[2-(2-benzyloxy-pyridin-3-yl)-4-tert-butyl-5-methoxy-benzyl]-3-methyl-1,3-dihydro-benzoimidazol-2-one (98).

Workup

  1. customstep 2—A sealed tube
  2. customwas irradiated on a microwave synthesizer at 100° 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-9be209afd859421290d5da2f0e92e3e1
Source dataset
uspto-grants-2012_07
Patent number
US08232271B2

Reaction notes

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