Bromide ion → HCID 2196908, compound

HRID 1297752Notes

Reaction equation

HRID 1297752 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].C(N=P1(N(CC)CC)N(C)CCCN1C)(C)(C)C.[Cl:31][C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH2:34]Br.[Br-]>C(#N)C.CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:34][C:33]1[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=1[Cl:31])[C:6](=[O:11])[C:5]2=[O:12]

Participants

7

Reactant 4

HCID 259Bromide ionHCID 68895-BromoisatinHCID 11905alpha-Bromo-o-chlorotolueneHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine

Product 1

HCID 2196908HCID 2196908, compoundYield 102.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

Partially dissolve 5-bromoisatin (45 mg, 0.20 mmol) in acetonitrile (2 mL) and add 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine on polysteyrene (95 mg, 0.21 mmol, 2.2 mmol/g, Fluka) followed by adding 2-chlorobenzyl bromide (0.026 mL, 0.20 mmol). Stir 18 h and add additional base (50 mg) and bromide (0.010 mL) to drive reaction to completion after another 3 h. Dilute with MeOH and warm with heat gun to insure soluability. Filter off beads and concentrate the filtrate in vacuo to obtain 72 mg of the title compound as a dark orange solid. Use material in subsequent reaction without further purification.

Workup

  1. customreaction to completion after another 3 h
  2. temperaturewarm
  3. temperaturewith heat gun
  4. filtrationFilter off beads
  5. concentrationconcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-224038ae9193406cbce8829088f86046
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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