Dimethylformamide → 3-(4-Oxo-7-pyrrol-1-yl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-benzamide

HRID 1266835Notes

Reaction equation

HRID 1266835 reaction equation
I[C:2]1[CH:3]=[C:4]([C:8]2[CH2:14][C:13](=[O:15])[NH:12][C:11]3[CH:16]=[C:17]([N:20]4[CH:24]=[CH:23][CH:22]=[CH:21]4)[CH:18]=[CH:19][C:10]=3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C[N:45]([CH:47]=[O:48])C>CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:15]=[C:13]1[CH2:14][C:8]([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[C:47]([NH2:45])=[O:48])=[N:9][C:10]2[CH:19]=[CH:18][C:17]([N:20]3[CH:24]=[CH:23][CH:22]=[CH:21]3)=[CH:16][C:11]=2[NH:12]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 185487204-(3-Iodo-phenyl)-8-pyrrol-1-yl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Product 1

HCID 185487603-(4-Oxo-7-pyrrol-1-yl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-benzamide

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-(3-iodo-phenyl)-8-pyrrol-1-yl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example 7) (214 mg, 0.5 mmol), Pd(OAc)2 (4 mg, 3 mol %), PPh3 (8mg, 8 mol %) and HDMS (0.52 mL, 2.5 mmol) in DMF (2 mL) was stirred under CO atmosphere at 60° C. for 4 h. The mixture was taken up in EtOAc, washed with 1 N HCl, sat. NaHCO3-sol. and brine, dried over MgSO4. Removal of the solvent in vacuum left a dark brown solid, which was purified by silica gel column chromatography with EtOAc/MeOH 95:5. Obtained as a yellow-brown solid (97 mg).

Workup

  1. washwashed with 1 N HCl, sat. NaHCO3-sol
  2. dry with materialand brine, dried over MgSO4
  3. customRemoval of the solvent in vacuum
  4. waitleft a dark brown solid, which
  5. customwas purified by silica gel column chromatography with EtOAc/MeOH 95:5

Sources & evidence

ORD record
ord-3cc42eb5a367435eb7c0840b0c9dc767
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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