Acetic Acid → HCID 91336602, compound

HRID 857376Notes

Reaction equation

HRID 857376 reaction equation
[Br:1][C:2]1[C:3]2[C:4]([S:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)=[C:5]3[CH:15]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:14][CH2:13][N:6]3[C:7]=2[CH:8]=[C:9]([C:11]#[N:12])[CH:10]=1.[N:29]([Sn](CCCC)(CCCC)CCCC)=[N+:30]=[N-:31].CC(O)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]2[C:4]([S:21][C:22]3[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=3)=[C:5]3[CH:15]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:14][CH2:13][N:6]3[C:7]=2[CH:8]=[C:9]([C:11]2[N:29]=[N:30][NH:31][N:12]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4984872Tributyltin azideHCID 91011404HCID 91011404, compound

Product 1

HCID 91336602HCID 91336602, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (+/−)-methyl {8-bromo-9-[(4-chlorophenyl)thio]-6-cyano-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl}acetate (example 31, Step 1, 200 mg, 0.42 mmol) in toluene (3 mL) was added azidotributyltin (279 mg, 0.84 mmol). The reaction mixture was stirred at 90° C. for 16 hours, AcOH (1 mL) was added and the reaction was stirred for 2 hours and concentrated. The residue was swished in acetone/hexane 1:2 to give 160 mg of the title compound as a white solid used as such for next reaction.

Workup

  1. stirringthe reaction was stirred for 2 hours
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-3fecb1f19e344226a919d3434e658e1f
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

Loading…