Sodium hydride → HCID 66956543, compound

HRID 2066683Notes

Reaction equation

HRID 2066683 reaction equation
[N+:1]([C:4]1[N:5]=[C:6]2[N:11]([CH:12]=1)[CH2:10][CH:9]([CH2:13][OH:14])[CH2:8][O:7]2)([O-:3])=[O:2].[I:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1.[H-].[Na+]>>[I:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][O:14][CH2:13][CH:9]2[CH2:8][O:7][C:6]3=[N:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][N:11]3[CH2:10]2)=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 9542584-Iodobenzyl bromideHCID 66956639HCID 66956639, compound

Product 1

HCID 66956543HCID 66956543, compoundYield 42%

Procedure

Alkylation of oxazine alcohol 180 (see Example 2MMM) with 4-iodobenzyl bromide and NaH (1.4 equiv.) as in Example 2UU above for 3 h, followed by chromatography of the product on silica gel, eluting with 0-1% EtOAc/CH2Cl2 (foreruns) and then with 3% EtOAc/CH2Cl2, gave 6-{[(4-iodobenzyl)oxy]methyl}-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (183) (42%) as a white solid: mp (CH2Cl2/hexane) 161-163° C.; 1H NMR (CDCl3) δ 7.70 (dt, J=8.3, 2.0 Hz, 2H), 7.40 (s, 1H), 7.03 (br d, J=8.3 Hz, 2H), 4.50 (ddd, J=11.4, 3.3, 0.8 Hz, 1H), 4.46 (s, 2H), 4.34 (dd, J=11.4, 7.8 Hz, 1H), 4.13 (ddd, J=12.3, 5.6, 0.8 Hz, 1H), 4.00 (dd, J=12.3, 7.6 Hz, 1H), 3.59 (dd, J=9.6, 5.8 Hz, 1H), 3.53 (dd, J=9.6, 6.5 Hz, 1H), 2.65 (m, 1H); HRFABMS calcd for C14H15IN3O4 m/z [M+H]+ 416.0107. found 416.0108.

Workup

  1. customabove for 3 h
  2. washeluting with 0-1% EtOAc/CH2Cl2 (foreruns)

Sources & evidence

ORD record
ord-46cad7a336ab42ce84af10284d879ab3
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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