Sodium hydride → HCID 66955654, compound

HRID 2066660Notes

Reaction equation

HRID 2066660 reaction equation
[CH3:1][C:2]1([CH2:14][OH:15])[O:7][C:6]2=[N:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][N:5]2[CH2:4][CH2:3]1.[I:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Br.[H-].[Na+]>>[I:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][O:15][CH2:14][C:2]1([CH3:1])[O:7][C:6]2=[N:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][N:5]2[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 27593613-Iodobenzyl bromideHCID 66955363HCID 66955363, compound

Product 1

HCID 66955654HCID 66955654, compoundYield 69%

Procedure

Alkylation of oxazine alcohol 149 (see Example 2OO) with 3-iodobenzyl bromide (1.6 equiv.) and NaH (1.8 equiv.) as in Example 2UU above for 3.5 h, followed by chromatography of the product on silica gel, eluting with CH2Cl2 (foreruns) and then with 0-2% EtOAc/CH2Cl2, gave 7-{[(3-iodobenzyl)oxy]methyl}-7-methyl-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (155) (69%) as a cream solid: mp (CH2Cl2/pentane) 122-125° C. (dec); 1H NMR (CDCl3) δ 7.63 (br d, J=7.9 Hz, 1H), 7.58 (m, 1H), 7.40 (s, 1H), 7.19 (br d, J=7.7 Hz, 1H), 7.06 (t, J=7.7 Hz, 1H), 4.49 (s, 2H), 4.11 (ddd, J=12.4, 7.3, 5.8 Hz, 1H), 4.01 (ddd, J=12.5, 6.7, 6.0 Hz, 1H), 3.63 (d, J=10.2 Hz, 1H), 3.60 (d, J=10.2 Hz, 1H), 2.37 (ddd, J=14.4, 6.7, 6.0 Hz, 1H), 2.12 (ddd, J=14.4, 7.3, 6.0 Hz, 1H), 1.47 (s, 3H). Anal. (C15H16IN3O4) C, H, N.

Workup

  1. customabove for 3.5 h
  2. washeluting with CH2Cl2 (foreruns)

Sources & evidence

ORD record
ord-905826748b344c4da523413e17005024
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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