Methanol → HCID 71115280, compound

HRID 1403676Notes

Reaction equation

HRID 1403676 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-4350c83938ae484cbdb156a8382229fc
Source dataset
uspto-grants-2014_12
Patent number
US08912209B2

Reaction notes

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