Sodium hydride → HCID 86650554, compound

HRID 2066681Notes

Reaction equation

HRID 2066681 reaction equation
Br[C:2]1[N:3]([CH2:10][CH:11]([CH2:14][O:15][C:16]2[CH:17]=[N:18][C:19]([Br:22])=[CH:20][CH:21]=2)[CH2:12][OH:13])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+]>>[Br:22][C:19]1[N:18]=[CH:17][C:16]([O:15][CH2:14][CH:11]2[CH2:12][O:13][C:2]3=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]3[CH2:10]2)=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 24758Sodium hydrideHCID 86650552HCID 86650552, compound

Product 1

HCID 86650554HCID 86650554, compoundYield 71%

Procedure

Ring closure of alcohol 190 with NaH (1.35 equiv.) as in Example 2GGG for 200 min, followed by chromatography of the product on silica gel, eluting with 0-1% MeOH/CH2Cl2 (foreruns) and then with 1-3% MeOH/CH2Cl2, gave 6-{[(6-bromo-3-pyridinyl)oxy]methyl}-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (191) (71%) as a pale yellow solid: mp (MeOH/CH2Cl2/hexane) 197-199° C.; 1H NMR [(CD3)2SO] δ 8.15 (br d, J=3.0 Hz, 1H), 8.10 (s, 1H), 7.56 (dd, J=8.7, 0.3 Hz, 1H), 7.42 (dd, J=8.8, 3.2 Hz, 1H), 4.60 (dd, J=11.0, 2.7 Hz, 1H), 4.45 (dd, J=11.0, 7.0 Hz, 1H), 4.29 (dd, J=12.5, 5.5 Hz, 1H), 4.20 (dd, J=10.0, 6.8 Hz, 1H), 4.17 (dd, J=10.0, 6.711z, 1H), 4.05 (dd, J=12.6, 6.8 Hz, 1H), 2.85 (m, 1H). Anal. (C12H11BrN4O4) C, H, N.

Workup

  1. customfor 200 min
  2. washeluting with 0-1% MeOH/CH2Cl2 (foreruns)

Sources & evidence

ORD record
ord-7b24c35aede44f21b5e44dc452fb7029
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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