Indole → 3-Cyanoindole

HRID 1975963Notes

Reaction equation

HRID 1975963 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 then be taken to the final product No. 138 in an analogous fashion to that shown in scheme 4.

Sources & evidence

ORD record
ord-f823e02406d14ac7a961dcdb8fe75de5
Source dataset
uspto-grants-2001_05
Patent number
US06225308B1

Reaction notes

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