Pyridine → HCID 86689037, compound

HRID 2175645Notes

Reaction equation

HRID 2175645 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 82.4%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (5.6 g, 20.0 mmol), 3-nitrophenylboronic acid (5.0 g, 30.0 mmol), Cu(OAc)2 (3.6 g, 20.0 mmol), pyridine (9.5 g, 120.0 mmol) and 4 Å MS (10.0 g) in dry DCM (150 mL) was purged with O2 before stirred at r.t. for 5 days. The reaction mixture was filtered through a celite pad and the filter cake was thoroughly washed with DCM. The filtrate was concentrated and purified by column chromatographic (silica gel, 0 to 50% DCM in PE during 15 min and then 0 to 20% ethyl acetate in a mixture of PE & DCM (1:1)) to afford 4-chloro-5-iodo-7-(3-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidine (16) (6.6 g, 82% yield) as a white solid. LC-MS (ESI): m/z (M/M+2) 399.9/400.9.

Workup

  1. customwas purged with O2
  2. filtrationThe reaction mixture was filtered through a celite pad
  3. washthe filter cake was thoroughly washed with DCM
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatographic (silica gel, 0 to 50% DCM in PE during 15 min
  6. addition0 to 20% ethyl acetate in a mixture of PE & DCM (1:1))

Sources & evidence

ORD record
ord-65b632ea66ab4ca89ff036cd72c37d30
Source dataset
uspto-grants-2015_06
Patent number
US09062058B2

Reaction notes

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