Sodium Carbonate → HCID 68591720, compound

HRID 1517545Notes

Reaction equation

HRID 1517545 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][C:8](=[O:11])[N:7]1[CH2:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:15][C:14]=1Br)=[O:5])[CH3:2].[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>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][C:8](=[O:11])[N:7]1[CH2:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:15][C:14]=1[C:39]1[C:34]([O:33][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[N:35][CH:36]=[CH:37][CH:38]=1)=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 44755161[2-(Benzyloxy)pyridin-3-yl]boronic acidHCID 68591281HCID 68591281, compound

Product 1

HCID 68591720HCID 68591720, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

step 2—A sealed tube containing 100 (150 mg, 0.36 mmol), 2-benzyloxy-pyridin-3-yl boronic acid (125 mg, 0.56 mmol), Na2CO3 (116 mg, 1.1 mmol) and Pd(PPh3)4 (42 mg, 0.036 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 50% EtOAc/hexanes to afford 140 mg (84%) of (R)-1-[2-(2-benzyloxy-pyridin-3-yl)-4-tert-butyl-5-methoxy-benzyl]-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester (102).

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-87f800e28c444f3fb566bd5e8a8e21b7
Source dataset
uspto-grants-2012_07
Patent number
US08232271B2

Reaction notes

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