Methanol → HCID 71115280, compound

HRID 2409374Notes

Reaction equation

HRID 2409374 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:23])[NH:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1Br)([CH3:4])([CH3:3])[CH3:2].[C:26]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)([OH:28])=[O:27].C([O-])([O-])=O.[Na+].[Na+].CO>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([O:5][C:6]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:23])[NH:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[C:33]1[CH:32]=[CH:31][CH:30]=[C:29]([C:26]([OH:28])=[O:27])[CH:34]=1)=[O:25])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 27339573-Carboxyphenylboronic acidHCID 67411147HCID 67411147, compound

Product 1

HCID 71115280HCID 71115280, compoundYield 70.2%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of Intermediate 16 (35 g, 0.086 mol, 1.0 eq) and 3-carboxyphenylboronic acid (14.27 g, 0.086, 1.0 eq) in DMF (350 ml) and H2O (87.5 ml) was added Na2CO3 (18.2 g, 0.172 mol, 2.0 eq). Then Pd(dppf)Cl2 (3.15 g, 0.0043 mol, 0.05 eq) was added to the solution under N2. The resulting solution was stirred at 100° C. for 16 hrs. Solvent was evaporated under vacuum and the residue was purified by column chromatography on silica gel using DCM: MeOH=10:1 to give the title compound (27 g, 70% yield) as brown solid.

Workup

  1. customSolvent was evaporated under vacuum
  2. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-db4a2faec19940b2aa93bde6c40b64f4
Source dataset
uspto-grants-2014_08
Patent number
US08815873B2

Reaction notes

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