2-Formylphenylboronic acid → HCID 86604965, compound

HRID 1714026Notes

Reaction equation

HRID 1714026 reaction equation
Br[C:2]1[N:3]([CH2:21][CH:22]([O:25][CH3:26])[O:23][CH3:24])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2.[CH:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O)=[O:28]>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH:11]1([C:10]2[C:9]3[C:4](=[CH:5][C:6]([C:17]([O:19][CH3:20])=[O:18])=[CH:7][CH:8]=3)[N:3]([CH2:21][CH:22]([O:25][CH3:26])[O:23][CH3:24])[C:2]=2[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[CH:27]=[O:28])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 2

HCID 2921892-Formylphenylboronic acidHCID 66674541HCID 66674541, compound

Product 1

HCID 86604965HCID 86604965, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 2-bromo-3-cyclohexyl-1-(2,2-dimethoxyethyl)-1H-indole-6-carboxylate (0.16 M, 1 eq, from Step 1) in dioxane and Na2CO3 (6 eq of a 2M solution) was degassed by sonication for 10 min. 2-Formylphenylboronic acid (1.5 eq) and bis(triphenylphosphine) palladium(II)dichloride (20 mol %) were added and the reaction placed in a pre-heated oil bath at 108° C. for 20 min. After cooling to RT, the reaction was partitioned between H2O and EtOAc (×3). The combined organics were washed with HCl (1N), H2O, and brine before being dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash column chromatography (Biotage, 10% EtOAc/PE) gave the title compound as a pale yellow solid (85%); MS (ES+) m/z 472 (M+Na)+, 450 (M+H)+.

Workup

  1. customthe reaction was partitioned between H2O and EtOAc (×3)
  2. washThe combined organics were washed with HCl (1N), H2O, and brine
  3. dry with materialbefore being dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (Biotage, 10% EtOAc/PE)

Sources & evidence

ORD record
ord-58f660dc8b65430091c45d723ae84cb4
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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