Cyanoacetic acid → HCID 57796681, compound

HRID 2099952Notes

Reaction equation

HRID 2099952 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[S:11][C:10]([CH:12]=O)=[CH:9][CH:8]=2)=[CH:5][CH:4]=[C:3]1[C:14]1[CH:15]=[C:16]2[C:24](=[CH:25][CH:26]=1)[N:23]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:22]1[CH:21]=[CH:20][C:19]([N:33]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:18][C:17]2=1.[C:46]([CH2:48][C:49]([OH:51])=[O:50])#[N:47]>C(O)(=O)C.C([O-])(=O)C.[NH4+]>[C:46](/[C:48](=[CH:12]\[C:10]1[S:11][C:7]([C:6]2[N:2]([CH3:1])[C:3]([C:14]3[CH:15]=[C:16]4[C:24](=[CH:25][CH:26]=3)[N:23]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:22]3[CH:21]=[CH:20][C:19]([N:33]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[C:40]5[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=5)=[CH:18][C:17]4=3)=[CH:4][CH:5]=2)=[CH:8][CH:9]=1)/[C:49]([OH:51])=[O:50])#[N:47]

Participants

5

Reactant 2

HCID 9740Cyanoacetic acidHCID 57796684HCID 57796684, compound

Product 1

HCID 57796681HCID 57796681, compound

Reagents, catalysts & solvents 2

HCID 517165Ammonium AcetateCatalystHCID 176Acetic AcidSolvent

Procedure

As shown in scheme 3, 3,6-dibromo-9-hexyl-9H-carbazole (31) is reacted with 1-methyl-2-(tributylstannyl)-1H-pyrrole by Stille coupling reaction to obtain N-methyl-2-(3-bromo-9-hexyl-9H-carbazol-6-yl)pyrrole (32). Then, in the presence of sodium tert-butoxide, Pd(dba)2, and tri-tert-butyl phosphine, N-methyl-2-(3-bromo-9-hexyl-9H-carbazol-6-yl)pyrrole (32) is reacted with diphenylamine to obtain N-methyl-2-(3-diphenylamino-9-hexyl-9H-carbazol-6-yl)pyrrole (33). n-butyl lithium is reacted with N-methyl-2-(3-diphenylamino-9-hexyl-9H-carbazol-6-yl)pyrrole (33), and then tributylstannylchloride is added thereto to obtain N-methyl-2-(3-diphenylamino-9-hexyl-9H-carbazol-6-yl)-5-tributyl-stannylpyrrole (34). N-methyl-2-(3-diphenylamino-9-hexyl-9H-carbazol-6-yl)-5-tributylstannylpyrrole (34) is reacted with 5-bromo-2-thiophene-carboxaldehyde by Stille coupling reaction to obtain 5-[N-methyl-2-(3-diphenylamino-9-hexyl-9H-carbazol-6-yl)pyrrol-5-yl]thiophene-2-carbaldehyde (35). Finally, 5-[N-methyl-2-(3-diphenylamino-9-hexyl-9y-carbazol-6-yl)pyrrol-5-yl]thiophene-2-carbaldehyde (35) is reacted with cyanoacetic acid in acetic acid by using ammonium acetate as a catalyst, and (E)-2-cyano-3-[5-(N-methyl-2-(3-diphenylamino-9-hexyl-9H-carbazol-6-yl)pyrrol-5-yl)thiophen-2-yl]acrylic acid (36) is obtained.

Sources & evidence

ORD record
ord-b379cb4dcede42da8c4d7bc48874b59b
Source dataset
uspto-grants-2009_08
Patent number
US07569704B1

Reaction notes

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