Ethyl Bromide → HCID 86633913, compound

HRID 1041050Notes

Reaction equation

HRID 1041050 reaction equation
[CH3:1][O:2][C:3]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:6]2[NH:7][C:8](=[O:18])[CH2:9][N:10]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:11][C:5]=2[CH:4]=1.[F-].[Cs+].[CH2:26](Br)[CH3:27].C(#N)C>[I-].[Na+]>[CH2:26]([N:7]1[C:6]2[CH:19]=[C:20]([N+:21]([O-:23])=[O:22])[C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH2:11][N:10]([C:12](=[O:17])[C:13]([F:14])([F:15])[F:16])[CH2:9][C:8]1=[O:18])[CH3:27]

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 6342AcetonitrileHCID 25953Cesium fluorideHCID 86633914HCID 86633914, compound

Product 1

HCID 86633913HCID 86633913, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 5238Sodium IodideCatalyst

Conditions

Temperature
45 °C

Procedure

A mixture of 7-Methoxy-8-nitro-4-(2,2,2-trifluoro-acetyl)-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (0.640 g, 0.00192 mol), Cesium fluoride (0.580 g, 0.00382 mol), Ethyl bromide (0.860 mL, 0.0116 mol) and Sodium iodide (0.0014 g, 0.0000093 mol) in Acetonitrile (15.0 mL, 0.287 mol) was heated at 45° C. for 8 hr. The reaction was evaporated, taken up in DCM/water, separated, washed, dried and evaporated to give 1-Ethyl-7-methoxy-8-nitro-4-(2,2,2-trifluoro-acetyl)-1,3,4,5-tetrahydro-benzo[e][1,4]diazepinone as a solid (0.59 g, 85%). Mp 128-129° C.; LCMS (m/e) 362 (M+1); 1H-NMR (DSMO, 400 MHz) δ 8.07 (d, 1H), 7.95 (s, 0.5H), 7.67 (s, 1H), 7.53 (s, 0.5H), 4.69 (s, 1H), 4.06 (s, 0.5H), 4.00 (s, 1H), 3.95 (s, 1H), 3.91-89 (q, 2H), 1.08-04 (t, 3H).

Workup

  1. customThe reaction was evaporated
  2. customseparated
  3. washwashed
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-41fb3130ee034153afe96f219b385ecc
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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