HCID 58204737, compound → HCID 58204828, compound

HRID 1498440Notes

Reaction equation

HRID 1498440 reaction equation
C([Mg]Cl)(C)C.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:12]([C:18](I)=[C:19]([I:21])[N:20]=3)[CH2:13][CH2:14][O:15][C:16]=2[N:17]=1>O1CCCC1>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:12]([CH:18]=[C:19]([I:21])[N:20]=3)[CH2:13][CH2:14][O:15][C:16]=2[N:17]=1

Participants

4

Reactant 2

HCID 58204737HCID 58204737, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 58204828HCID 58204828, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
15 °C

Procedure

2.0 M of Isopropylmagnesium Chloride in tetrahydrofuran (0.782 mL) was added dropwise to a solution of 0.644 g (1.36 mmol) of 9-chloro-2,3-diiodo-5,6-dihydroimidazo[1,2-d]pyrido[3,2-f][1,4]oxazepine in 12 ml of tetrahydrofuran at −10° C. The mixture was allowed to warm to 15° C. The mixture then was quenched by addition of 20 ml of sat. aqueous NH4Cl and extracted with ethyl acetate. The organic extracts were washed with water, brine, dried over Na2SO4 and concentrated to give 9-chloro-2-iodo-5,6-dihydroimidazo[1,2-d]pyrido[3,2-f][1,4]oxazepine. Yield 448 mg (98%). M/z 348.2, calc. M 346.93. 1H NMR (400 MHz, CDCl3) δ 8.83 (d, J=8.2, 1H), 7.16 (dd, J=14.0, 5.9, 1H), 7.10 (s, 1H), 4.61-4.54 (m, 2H), 4.41 (dd, J=5.0, 2.9, 2H)

Workup

  1. customThe mixture then was quenched by addition of 20 ml of sat. aqueous NH4Cl
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-75e51be179db4a6e86a831f787a346bd
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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