Sodium hydride → HCID 86650549, compound

HRID 2066659Notes

Reaction equation

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

Participants

Reactant 2

HCID 24758Sodium hydride

HCID 86650548HCID 86650548, compound

Product 1

HCID 86650549HCID 86650549, compoundYield 66%

Procedure

Ring closure of alcohol 151 with NaH (1.5 equiv.) as in Example 2AA, followed by chromatography of the product on silica gel, eluting with 0-50% EtOAc/petroleum ether (foreruns) and then with 0-2% MeOH/CH2Cl2, gave 7-{[(6-bromo-3-pyridinyl)oxy]methyl}-7-methyl-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (152) (66%) as a light yellow solid: mp (CH2Cl2/hexane) 170-171° C.; 1H NMR (CDCl3) δ 8.06 (dd, J=3.1, 0.3 Hz, 1H), 7.46 (s, 1H), 7.40 (dd, J=8.7, 0.3 Hz, 1H), 7.11 (dd, J=8.7, 3.2 Hz, 1H), 4.21-4.07 (m, 4H), 2.52 (ddd, J=14.5, 8.1, 6.3 Hz, 1H), 2.24 (dt, J=14.5, 5.7 Hz, 1H), 1.60 (s, 3H). Anal. (C13H13BrN4O4) C, H, N.

Workup

washeluting with 0-50% EtOAc/petroleum ether (foreruns)

Sources & evidence

ORD record: ord-f3ade3996dc44b21892e6efb6a4b947a
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293734B2

Reaction notes

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