Triphenylphosphine → HCID 42635877, compound

HRID 1873355Notes

Reaction equation

HRID 1873355 reaction equation
[OH:1][CH2:2][CH2:3][O:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[Br:15][C:16]1[CH:17]=[CH:18][C:19]2[N:20]([CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=3)[N:24]=2)[CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)(Cl)Cl.CN(C)C=O>[Br:15][C:16]1[CH:17]=[CH:18][C:19]2[N:20]([CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([O:1][CH2:2][CH2:3][O:4][S:5]([C:8]4[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=4)(=[O:7])=[O:6])=[CH:27][CH:26]=3)[N:24]=2)[CH:21]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 2491552-hydroxyethyl 4-methylbenzenesulfonateHCID 5363146Diisopropyl azodicarboxylateHCID 24864014HCID 24864014, compound

Product 1

HCID 42635877HCID 42635877, compoundYield 12.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

To 10 mL of a solution of 639 mg (corresponding to 2.95 mmol) of 2-hydroxyethyl-p-toluenesulfonate in tetrahydrofran, 388 mg (corresponding to 1.34 mmol) of 6-bromo-2-(4′-hydroxyphenyl)imidazo[1,2-a]pyridine and 780 mg (corresponding to 2.97 mmol) of triphenylphosphine were added. Further, 6 mL of N,N-dimethylformamide was added thereto to completely dissolve the contents. To the reaction mixture, 0.58 mL (corresponding to 2.95 mmol) of diisopropylazodicarboxylate was added. After the reaction mixture was stirred at room temperature for 17 hours, the reaction solution was concentrated. The resulting crude product was purified by flash silica gel column chromatography (elution solvent: hexane/ethyl acetate=65/35). Insoluble matter in chloroform was filtered out of fractions containing a target compound. Further, the resulting crude product was purified by recycle preparative HPLC (HPLC apparatus: LC-908 (under trade name; manufactured by Japan Analytical Industry Co., Ltd.); column: two JAIGEL 2H (under trade name; manufactured by Japan Analytical Industry Co., Ltd.) connected together; mobile phase: chloroform), to obtain 79.7 mg (corresponding to 164 μmol) of 6-bromo-2-[4′-(2″-p-toluenesulfonyloxyethoxy)phenyl]imidazo[1,2-a]pyridine (FIG. 1-3, Step 4).

Workup

  1. dissolutionto completely dissolve the contents
  2. concentrationthe reaction solution was concentrated
  3. customThe resulting crude product was purified by flash silica gel column chromatography (elution solvent: hexane/ethyl acetate=65/35)
  4. filtrationInsoluble matter in chloroform was filtered out of fractions
  5. additioncontaining a target compound
  6. customFurther, the resulting crude product was purified by recycle preparative HPLC (HPLC apparatus

Sources & evidence

ORD record
ord-ce964345e486457e971f719b553cf7d8
Source dataset
uspto-grants-2012_11
Patent number
US08303935B2

Reaction notes

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