1,2-Dimethoxyethane → HCID 50938851, compound

HRID 1971671Notes

Reaction equation

HRID 1971671 reaction equation
Br[C:2]1[C:3]([O:31][CH3:32])=[CH:4][C:5]2[CH2:6][CH2:7][N:8]3[CH:14]4[C:15](=[O:25])[N:16]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:17][CH2:18][S:19][CH2:20][CH:13]4[C:12]([C:26]4[S:27][CH:28]=[CH:29][CH:30]=4)=[C:9]3[C:10]=2[CH:11]=1.[N:33]1[CH:38]=[CH:37][CH:36]=[C:35](B(O)O)[CH:34]=1.C([O-])([O-])=O.[K+].[K+].C(COC)OC>O.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>[C:21]([N:16]1[C:15](=[O:25])[CH:14]2[CH:13]([C:12]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[C:9]3[C:10]4[CH:11]=[C:2]([C:35]5[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=5)[C:3]([O:31][CH3:32])=[CH:4][C:5]=4[CH2:6][CH2:7][N:8]32)[CH2:20][S:19][CH2:18][CH2:17]1)([CH3:23])([CH3:22])[CH3:24]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 58124936HCID 58124936, compound

Product 1

HCID 50938851HCID 50938851, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture containing 20 mg of 9j, 6 mg of pyridine-3-boronic acid and 10 mg of K2CO3 and 6 mg of Pd(PPh3)4 in 2 ml of degassed 90% aq. dimethoxyethane was heated under N2 for 16 h. The reaction mixture was cooled and diluted with water. The product was extracted with ethyl acetate. The extract was dried, concentrated and the residue was purified by chromatography over silica gel, using heptane/acetone as eluent. The isolated product was treated with ether/ethyl acetate (9/1 v/v) to give 14 mg of white crystalline 9k; Rf 0.50 (heptane/acetone 1/1);

Workup

  1. temperaturewas heated under N2 for 16 h
  2. temperatureThe reaction mixture was cooled
  3. extractionThe product was extracted with ethyl acetate
  4. customThe extract was dried
  5. concentrationconcentrated
  6. customthe residue was purified by chromatography over silica gel
  7. additionThe isolated product was treated with ether/ethyl acetate (9/1 v/v)

Sources & evidence

ORD record
ord-66efe3109d9f4899abfb11f27a55bb64
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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