Dimethylformamide → 10-Bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 1530540Notes

Reaction equation

HRID 1530540 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][CH2:7][CH2:8][N:9]3[C:13]2=[N:12][C:11](I)=[CH:10]3)=[CH:4][CH:3]=1.C[Si](C)(C)N[Si](C)(C)C.C[N:27]([CH:29]=[O:30])C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][CH2:7][CH2:8][N:9]3[C:13]2=[N:12][C:11]([C:29]([NH2:27])=[O:30])=[CH:10]3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 13838HexamethyldisilazaneHCID 5820440710-Bromo-2-iodo-5,6-dihydrobenzo[F]imidazo[1,2-D][1,4]oxazepine

Product 1

HCID 6831288310-Bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 95%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
70 °C

Procedure

To a solution of 13-bromo-4-iodo-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene (5.0 g, 0.013 mol) in DMF (50 mL) was added hexamethyldisilazane (16 mL, 0.077 mol) and Pd(PPh3)2Cl2 (0.45 g, 0.639 mmol). After being purged with CO three times, the mixture was heated at 70° C. for 3 h. After removal of the solvent, water (100 mL) was added. The solid was collected by filtration, washed with water, and dried in vacuo to afford the title compound (3.8 g, 95% yield) as a yellow solid. LCMS m/z [M+H]+ 309.1.

Workup

  1. customAfter being purged with CO three times
  2. customAfter removal of the solvent, water (100 mL)
  3. additionwas added
  4. filtrationThe solid was collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-cd38935e151048df9bcdf0e499e05ff0
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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