Benzoyl chloride → HCID 21313377、化合物

反応式

COC1C=CC(NN)=CC=1.O=C(CCC)C(OCC)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].OCCC1C2C(=CC=C(OC)C=2)NC=1C.[H-].[Na+].[Na].C(Cl)(=O)C1C=CC=CC=1.[C:54]([N:62]1[C:70]2[C:65](=[CH:66][C:67]([O:71][CH3:72])=[CH:68][CH:69]=2)[C:64]([CH2:73][CH2:74]O)=[C:63]1[CH3:76])(=[O:61])[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1.S(Br)([Br:79])=O.C(=O)([O-])[O-].[Ca+2]>C(O)C.O1CCCC1.CN(C=O)C.C1C=CC=CC=1>[C:54]([N:62]1[C:70]2[C:65](=[CH:66][C:67]([O:71][CH3:72])=[CH:68][CH:69]=2)[C:64]([CH2:73][CH2:74][Br:79])=[C:63]1[CH3:76])(=[O:61])[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1

参加物

実験手順

Reaction of 4-methoxyphenylhydrazine with ethyl α-ketovalerate in ethanol using the procedure described above in Example 1; reduction with lithium aluminum hydride in tetrahydrofuran of the resulting ethyl α-(5-methoxy-2-methyl-3-indole)acetate; reaction of the resulting 3-(2-hydroxyethyl)-5-methoxy-2-methylindole with sodium hydride in DMF, and reaction of the resulting sodium salt with benzoyl chloride using the procedure described above in Example 1; and reaction of the resulting 1-benzoyl-3-(2-hydroxyethyl)-5-methoxy-2-methylindole with thionyl bromide in benzene in the presence of calcium carbonate using the procedure described in U.S. Pat. No. 3,517,028 affords 1-benzoyl-3-(2-bromoethyl)-5-methoxy-2-methylindole. The latter, on reaction with an appropriate amine in refluxing acetone in the presence of sodium carbonate affords the compounds of formula I in Examples 72-77 below where, in each instance, R1 is 5-CH3O; R2 is CH3 ; A is C6H5CO; and Alk is CH2CH2.

出典と根拠

ORDレコード: ord-a1028e1e6ec94301b95e62cf2b20881a
出典データセット: uspto-grants-1979_07
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US04160862

反応ノート

読み込み中…

反応式

参加物

反応物 10

生成物 1

試薬・触媒・溶媒 4

実験手順

出典と根拠

反応ノート