Pyridine → HCID 86689037, compound

HRID 920217Notes

Reaction equation

HRID 920217 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[N+:12]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].N1C=CC=CC=1>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:12]([O-:14])=[O:13])[CH:20]=3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 16773-Nitrophenylboronic AcidHCID 148092816-Chloro-7-iodo-7-deazapurine

Product 1

HCID 86689037HCID 86689037, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (5.58 g, 20 mmol) in DCM (200 mL) were added 3-nitrophenylboronic acid (5 g, 30 mmol), pyridine (9.49 g, 120 mmol), anhydrous Cu(OAc)2 (3.64 g, 20 mmol) and 4A MS (20 g). The resulting suspension was stirred at room temperature overnight under O2 atmosphere and then quenched with water and filtered through a pad of celite. The filtrate was concentrated under vacuum. The crude product was purified by flash chromatography (silica gel, 0-30% ethyl acetate in petroleum ether) to provide 4-chloro-5-iodo-7-(3-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidine (68) (5.9 g, 74%) as a yellow solid. LC-MS (ESI): m/z (M+1) 401.

Workup

  1. customquenched with water
  2. filtrationfiltered through a pad of celite
  3. concentrationThe filtrate was concentrated under vacuum
  4. customThe crude product was purified by flash chromatography (silica gel, 0-30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-9ca157dc1d3d4ad2a3b1f5384c15dab6
Source dataset
uspto-grants-2016_03
Patent number
US09273051B2

Reaction notes

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