Tetrahydrofuran → HCID 58479601, compound

HRID 1516999Notes

Reaction equation

HRID 1516999 reaction equation
[N:1]([C:4]1[C:5]([Cl:11])=[N:6][CH:7]=[CH:8][C:9]=1[I:10])=[N+]=[N-].[C:12]1([P:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1COCC1.[N-]=[N+]=[N-]>O>[Cl:11][C:5]1[C:4]([N:1]=[P:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:9]([I:10])[CH:8]=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 33558AzideHCID 149703923-Azido-2-chloro-4-iodopyridine

Product 1

HCID 58479601HCID 58479601, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-azido-2-chloro-4-iodopyridine (7 g, 25 mmol) and triphenylphosphine (8.5 g, 32 mmol) was stirred in 100 mL 1:1 mixture of THF and water until azide starting material disappears in TLC. After that most of the THF was removed under vacuum. Crude product was partitioned between brine and ethylacetate. Organic layer was isolated, dried over anhd. Na2SO4 and purified by silica gel column chromatography using 5-40% ethyl acetate and hexanes as eluent. 2-chloro-4-iodo-N-(triphenylphosphoranylidene)pyridin-3-amine (12 g, 23 mmol, 93% yield) was isolated as crystalline white solid.

Workup

  1. customAfter that most of the THF was removed under vacuum
  2. customCrude product was partitioned between brine and ethylacetate
  3. customOrganic layer was isolated
  4. customdried over anhd
  5. customNa2SO4 and purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3730f77377aa46a48bedceaedafdcddf
Source dataset
uspto-grants-2012_07
Patent number
US08227801B2

Reaction notes

Loading…