Ammonium Chloride → 10-Chloro-2-iodo-5,6-dihydroimidazo[1,2-d]pyrido[4,3-f][1,4]oxazepine

HRID 1498079Notes

Reaction equation

C([Mg]Cl)(C)C.[Cl:6][C:7]1[N:17]=[CH:16][C:15]2[O:14][CH2:13][CH2:12][N:11]3[C:18](I)=[C:19]([I:21])[N:20]=[C:10]3[C:9]=2[CH:8]=1.[NH4+].[Cl-]>O1CCCC1>[Cl:6][C:7]1[N:17]=[CH:16][C:15]2[O:14][CH2:13][CH2:12][N:11]3[CH:18]=[C:19]([I:21])[N:20]=[C:10]3[C:9]=2[CH:8]=1

Participants

Conditions

Temperature: 10 °C

Procedure

Isopropylmagnesium chloride in tetrahydrofuran (2.0 M, 3.311 mL) was added dropwise to a solution of 10-chloro-2,3-diiodo-5,6-dihydroimidazo[1,2-d]pyrido[4,3-f][1,4]oxazepine (2.850 g, 6.020 mmol) in 110 ml of tetrahydrofuran at −10° C. The mixture was allowed to warm to 10° C. in 45 min and then mixed with 250 ml of cold 10% NH4Cl. The organic layer was washed with brine and dried over Na2SO4. Concentration in vacuum afforded 2.06 g of 10-chloro-2-iodo-5,6-dihydroimidazo[1,2-d]pyrido[4,3-f][1,4]oxazepine (98.5%). MS: 348.0. 1H NMR (500 MHz, CDCl3) δ 8.33 (d, J=10.1, 1H), 8.18 (s, 1H), 7.18 (s, 1H), 4.46 (q, J=5.8, 4H).

Workup

washThe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationConcentration in vacuum

Sources & evidence

ORD record: ord-92548ee8451545b6b46976ddf36d1150
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09198918B2

Reaction notes

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