Boron tribromide → HCID 136355230, compound

HRID 1297121Notes

Reaction equation

HRID 1297121 reaction equation
B(Br)(Br)Br.C([O:7][C:8]1[C:9]([O:28]CC)=[CH:10][C:11]2[N:17]([CH2:18][CH3:19])[C:16](=[O:20])[CH2:15][N:14]=[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:12]=2[CH:27]=1)C>C(Cl)Cl>[CH2:18]([N:17]1[C:11]2[CH:10]=[C:9]([OH:28])[C:8]([OH:7])=[CH:27][C:12]=2[C:13]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[N:14][CH2:15][C:16]1=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 9924639HCID 9924639, compound

Product 1

HCID 136355230HCID 136355230, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add dropwise at 0° C. under an inert atmosphere, 0.68 ml of a 1 M solution of BBr3 (0.68 mmol) in CH2Cl2 on 200 mg (0.62 mmol) of 7,8-diethoxy-1-ethyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (IIbg) in 5 ml of dichloromethane. Stir at room temperature for 12 hours. Quench at 0° C. with methanol. Evaporate to dryness. Triturate again and evaporate. Purify by chromatography (AcOEt). Recrystallize in EtO2/pentane. One obtains 30 mg of the abovenamed product as a yellow powder. Yield: 16%. M: 230–231° C. 1H-NMR (DMSO, 200 MHz): d 0.96 (t, 3H, CH3), 3.80 (AB system, ? d=0.54, JAB=13.7, 2H, —NCH2), 4.05 (AB system, ? d=0.72, JAB=10.0, 2H, CH2), 6.52 (s, 1H Ar), 6.91 (s, 1H Ar), 7.42–7.55 (m, 5H Ar), 9–10.5 (hump, 2H, 2×—OH).

Workup

  1. customQuench at 0° C. with methanol
  2. customEvaporate to dryness
  3. customTriturate again
  4. customevaporate
  5. customPurify by chromatography (AcOEt)
  6. customRecrystallize in EtO2/pentane

Sources & evidence

ORD record
ord-564d0c2e8a8e42e3b0e8e787d6ef3c17
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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