Dimethylformamide → 9-Bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carbaldehyde

HRID 886031Notes

Reaction equation

HRID 886031 reaction equation
C([Mg]Br)C.[Br:5][C:6]1[CH:20]=[CH:19][C:9]2[C:10]3[N:11]([CH:15]=[C:16](I)[N:17]=3)[CH2:12][CH2:13][O:14][C:8]=2[CH:7]=1.CN(C)[CH:23]=[O:24]>C(OCC)C.O1CCCC1>[Br:5][C:6]1[CH:20]=[CH:19][C:9]2[C:10]3[N:11]([CH:15]=[C:16]([CH:23]=[O:24])[N:17]=3)[CH2:12][CH2:13][O:14][C:8]=2[CH:7]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 582048589-Bromo-2-iodo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepineHCID 178418443HCID 178418443, compound

Product 1

HCID 582043679-Bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
15 °C

Procedure

Ethylmagnesium bromide in ethyl ether (3.0 M, 3.472 mL) was added dropwise to a solution of 9-bromo-2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (1173 mg, 3.000 mmol) in 20 ml of tetrahydrofuran at −30° C. The mixture was stirred at this temperature for 20 min and allowed to warm to 15° C. The mixture was cooled to −25° C. again and N,N-dimethylformamide (929.2 uL, 12.00 mmol) was added. The mixture was left for 18 hours. The mixture was quenched with sat. aq. NH4Cl and extracted with ethyl acetate. The organic extracts were washed with water, brine, dried over mgSO4 and concentrated in vacuum. Yield 0.92 g. MS: 293.1

Workup

  1. temperatureThe mixture was cooled to −25° C. again
  2. waitThe mixture was left for 18 hours
  3. customThe mixture was quenched with sat. aq. NH4Cl
  4. extractionextracted with ethyl acetate
  5. washThe organic extracts were washed with water, brine
  6. customdried over mgSO4
  7. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-dc93d2de3dfa4e1da9853125c319d275
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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