Indole → 3-Cyanoindole

HRID 2308312Notes

Reaction equation

HRID 2308312 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 in DMF using sodium hydride to give the intermediate No. 157. This can be taken to the final product No. 138 in an analogous fashion to that shown in scheme 4.

Sources & evidence

ORD record
ord-0f538021ae8c493d8de8b30a64348ff1
Source dataset
uspto-grants-2004_12
Patent number
US06835729B2

Reaction notes

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