Pyridine → HCID 86689037, compound

HRID 388444Notes

Reaction equation

HRID 388444 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 4 A 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-282bc7e7007b4b31a608978a7e3d8796
Source dataset
uspto-grants-2013_02
Patent number
US08377946B1

Reaction notes

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