Triphenylphosphine → HCID 67528786, compound

HRID 1867553Notes

Reaction equation

HRID 1867553 reaction equation
[N:1]1([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17]O)=[CH:12][CH:11]=2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[O:19]1[CH2:23][C:22](=[O:24])[NH:21][C:20]1=[O:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1.CC(C)=O>[N:1]1([C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][N:21]3[C:22](=[O:24])[CH2:23][O:19][C:20]3=[O:25])=[CH:14][CH:15]=2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 973892,4-OxazolidinedioneHCID 67528572HCID 67528572, compound

Product 1

HCID 67528786HCID 67528786, compoundYield 112.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.0 g (4.20 mmol) of 2-[4-(1H-pyrrolo[2,3-b]pyridin-1-yl)phenyl]ethanol, prepared in step 13.1., 0.51 g (5.04 mmol) of 1,3-oxazolidine-2,4-dione and 1.21 g (4.62 mmol) of triphenylphosphine in 16 ml of tetrahydrofuran, cooled by a bath of acetone and ice, is admixed dropwise with 0.84 g (4.2 mmol) of diisopropyl azodicarboxylate in solution in 2 ml of tetrahydrofuran. The mixture is subsequently heated to ambient temperature again and stirred overnight. 4 g of silica are added and the mixture is evaporated to dryness. The residue is purified by chromatography on silica gel, eluting with a 70/30 then 60/40 then 50/50 and 40/60 mixture of cyclohexane and ethyl acetate, to give 1.52 g of product in the form of a sticky solid, which is used as it is in the following step.

Workup

  1. addition4 g of silica are added
  2. customthe mixture is evaporated to dryness
  3. customThe residue is purified by chromatography on silica gel
  4. washeluting with a 70/30
  5. addition60/40 then 50/50 and 40/60 mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-f0eb4adc32654774ab5ce5d00d12a18b
Source dataset
uspto-grants-2009_12
Patent number
US07632850B2

Reaction notes

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