Indole → 3-Cyanoindole

HRID 1005916Notes

Reaction equation

HRID 1005916 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 firm 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 in 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.

Sources & evidence

ORD record
ord-b0e4d6d7a1ed4b9fb0f896e5d5f23a4a
Source dataset
uspto-grants-2004_09
Patent number
US06787538B2

Reaction notes

Loading…