Dichloromethane → HCID 53874238, compound

HRID 1756074Notes

Reaction equation

HRID 1756074 reaction equation
[CH3:1][C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:11].[Br:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[CH2:15][CH2:16]Br.C(Cl)Cl>CC#N>[CH3:1][C:2]1[N:10]=[C:5]2[N:6]([CH2:16][CH2:15][C:14]3[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=3[Br:12])[CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:11]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 3340691-Bromo-2-(2-bromoethyl)benzeneHCID 125323872,3-Dimethyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 53874238HCID 53874238, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2,3-dimethylpyrrolo[2,3-b]pyridine (554 mg, 3.8 mmol) and o-bromophenethyl bromide (1000 mg, 3.8 mmol) in 11 ml CH3CN was refluxed for 16 h. The solvent was evaporated and the residue chromatographed (silica, CH2Cl2 /MeOH; 9/1) to give 546 mg enriched product. Pure 2,3-dimethyl-7-(o-bromophenethyl) pyrrolo[2,3-b]pyridine was obtained by a second chromatography (silica, CH2Cl2 saturated with NH3/petroleum ether; 7/3). A deaerated solution of 2,3-dimethyl-7- (o-bromophenethyl) pyrrolo[2,3-b]pyridine (249 mg, 0.76 mmol) in 25 ml dry THF was cooled to -78° C. and treated with 1.6M n-BuLi in hexane (576 μl, 0.91 mmol). After 3 min a vigurous stream of CO2 (g) was bubbled through the solution. The solution was allowed to warm to room temperature and 1.5 ml H2O was added. The solvent was evaporated and the residue chromatographed (reversed phase silica, MeOH/H2O; 6/4) yielding 51 mg (23%) pure amino acid.

Workup

  1. customThe solvent was evaporated
  2. customthe residue chromatographed (silica, CH2Cl2 /MeOH; 9/1)
  3. customto give 546 mg

Sources & evidence

ORD record
ord-4d78285b689e4daf8744ead461b07458
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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