2-Bromopyridine → 161229-62-5

HRID 1940512Notes

Reaction equation

HRID 1940512 reaction equation
[F:1][CH:2]([F:25])[C:3]1([CH:22]([F:24])[F:23])[CH2:8][N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[C:6]2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:5]=2[O:4]1.FC(F)C1(C(F)F)CNC2C=C([N+]([O-])=O)C=CC=2[O:29]1.C(=O)([O-])[O-].[K+].[K+].BrC1C=CC=CN=1.C1OCCOCCOCCOCCOCCOC1>ClCCl.[Cu].ClC1C=CC=CC=1Cl>[F:25][CH:2]([F:1])[C:3]1([CH:22]([F:24])[F:23])[CH2:8][N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N+:10]=2[O-:29])[C:6]2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:5]=2[O:4]1

Participants

9

Reactant 5

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 21462566HCID 21462566, compoundHCID 21462587HCID 21462587, compound

Product 1

HCID 9929430161229-62-5

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 6344DichloromethaneSolventHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
170 °C

Procedure

2-(2,2-bis(Difluoromethyl)-6-nitro-3,4-dihydro-2H-1,4-benzoxazine-4-yl)pyridine. The product of step c. (0.81 g) potassium carbonate (1.6 g), copper bronze (0.37 g), 2-bromopyridine (0.83 mL), 18-crown-6 (0.079 g), and 1,2-dichlorobenzene (8 mL) were stirred and heated at 170° C. for six hours. The reaction mixture was cooled, diluted with dichloromethane and chromatographed, eluting with dichloromethane, to give the pyridine as a light amber syrup (0.77 g); NMR: 4.34 (s,2), 6.55 (t,2), 7.07 (m,1), 7.37 (m,2), 7.82 (m,2), 8.23 (s,1), 8.39 (d,1); MS: m/z=358(M+1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customchromatographed
  3. washeluting with dichloromethane
  4. customto give the pyridine as a light amber syrup (0.77 g)

Sources & evidence

ORD record
ord-420fb9f415c04d20aaf8398239d9228e
Source dataset
uspto-grants-1997_12
Patent number
US05700798

Reaction notes

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