Water → HCID 57905906, compound

HRID 1670157Notes

Reaction equation

HRID 1670157 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:13]#[C:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[C:21]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[C:22]([CH:30]=[CH:31][CH:32]=2)[O:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])[CH:5]=[C:6]([C:8](=[O:12])[N:9]([CH3:11])[CH3:10])[CH:7]=1.O.[CH2:39]1[O:47][C:46]2[CH:45]=[CH:44][C:43](B(O)O)=[CH:42][C:41]=2[O:40]1.C(=O)([O-])[O-].[K+].[K+]>CCO.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>[O:40]1[C:41]2[CH:42]=[CH:43][C:44]([C:2]3[CH:3]=[C:4]([C:13]#[C:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]4[C:21]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[C:22]([CH:30]=[CH:31][CH:32]=4)[O:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])[CH:5]=[C:6]([C:8](=[O:12])[N:9]([CH3:11])[CH3:10])[CH:7]=3)=[CH:45][C:46]=2[O:47][CH2:39]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 57905901HCID 57905901, compound

Product 1

HCID 57905906HCID 57905906, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

To a solution of 4-[3-[7-(3-bromo-5-dimethylcarbamoyl-phenyl)-hept-6-ynyl]-2-(2-carboxy-ethyl)-phenoxy]-butyric acid (100 mg, 0.17 mmol) in EtOH (4 mL)/H2O (1 mL) were added 3,4-methylenedioxyphenylboronic acid (58 mg, 0.35 mmol), potassium carbonate (100 mg, 0.7 mmol) and Pd(PPh3)4 (5 mg, 0.004 mmol). The mixture was heated at 78° C. for 5 h and then cooled to room temperature. The reaction mixture was filtered using a syringe filter 0.45 μm and the filtrate concentrated under reduced pressure. The crude oil was then purified by preparative HPLC using acetonitrile/water gradient. HRMS calcd for C36H39NO8 [M+H]+ 614.2749, observed 614.2748

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe reaction mixture was filtered
  3. filtrationfilter 0.45 μm
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe crude oil was then purified by preparative HPLC

Sources & evidence

ORD record
ord-836d6ddb136f43d5b593c39d5ffde59f
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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