Sodium hydride → HCID 66956067, compound

HRID 2066676Notes

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].[Br:15][C:16]1[CH:17]=[CH:18][C:19](F)=[N:20][CH:21]=1.[H-].[Na+]>>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([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)=[N:20][CH:21]=1

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 27831685-Bromo-2-fluoropyridine

HCID 66956639HCID 66956639, compound

Product 1

HCID 66956067HCID 66956067, compoundYield 67%

Procedure

Alkylation of oxazine alcohol 180 with 5-bromo-2-fluoropyridine (91) (2.0 equiv.) and NaH (1.74 equiv.) as in Example 2OO for 3 h, followed by chromatography of the product on silica gel, eluting with 0-0.25% MeOH/CH2Cl2 (foreruns) and then with 0.25-0.5% MeOH/CH2Cl2, gave 6-{[(5-bromo-2-pyridinyl)oxy]methyl}-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (181) (67%) as a white solid: mp (MeOH/CH2Cl2/hexane) 233-235° C.; 1H NMR [(CD3)2SO] δ 8.27 (dd, J=2.5, 0.4 Hz, 1H), 8.07 (s, 1H), 7.93 (dd, J=8.8, 2.6 Hz, 1H), 6.85 (dd, J=8.9, 0.5 Hz, 1H), 4.60 (dd, J=11.0, 2.7 Hz, 1H), 4.44 (dd, J=11.1, 7.4 Hz, 1H), 4.36 (dd, J=11.0, 6.7 Hz, 1H), 4.33 (dd, J=11.0, 6.7 Hz, 1H), 4.27 (dd, J=12.5, 5.4 Hz, 1H), 4.04 (dd. J=12.6, 7.1 Hz, 1H), 2.85 (m, 1H). Anal. (C12H11BrN4O4.) C, H, N.

Workup

washeluting with 0-0.25% MeOH/CH2Cl2 (foreruns)

Sources & evidence

ORD record: ord-1257913e53d6419fbf5286188405939f
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293734B2

Reaction notes

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