Indole → 3-Cyanoindole

HRID 365588Notes

Reaction equation

HRID 365588 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.ClS([N:14]=[C:15]=O)(=O)=O>C(N(CC)CC)C>[C:15]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)#[N:14]

Participants

4

Reactant 2

HCID 798Indole2×HCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 2302823-Cyanoindole

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

3-Cyano analogues are synthesized from the precursor indole No. 141 as shown in Scheme 7. Reaction of the precursor indole No. 141 with chlorosulfonyl isocyanate followed by addition of triethylamine yields the 3-Cyanoindole No. 155. The side chain is made by conversion of the benzylic alcohol of CAS No. [111728-87-1] to the benzylic bromide No. 156 using thionyl bromide in THF. The indole is alkylated by the side chain DMF using sodium hydride to give the intermediate No. 157. This can then be taken to the final product No. 138 in an analogous fashion to that shown in scheme 4. ##STR13##

Sources & evidence

ORD record
ord-ac379e8894d945c6bbeb37e1d5dca883
Source dataset
uspto-grants-2000_10
Patent number
US06127404

Reaction notes

Loading…