Indole → 3-Cyanoindole

HRID 269860

반응식

HRID 269860 반응식
[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]

참가 물질

4

반응물 2

HCID 798Indole2회HCID 70918Chlorosulfonyl isocyanate

생성물 1

HCID 2302823-Cyanoindole

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

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.

출처 및 근거

ORD 기록
ord-35d9da6ac43345f28de0e1925b695821
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449455B2

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