5-Bromothiophene-2-carbaldehyde → HCID 57796684, compound

HRID 2099951Notes

Reaction equation

HRID 2099951 reaction equation
[CH3:1][N:2]1[C:6]([Sn](CCCC)(CCCC)CCCC)=[CH:5][CH:4]=[C:3]1[C:20]1[CH:21]=[C:22]2[C:30](=[CH:31][CH:32]=1)[N:29]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:28]1[CH:27]=[CH:26][C:25]([N:39]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:24][C:23]2=1.Br[C:53]1[S:57][C:56]([CH:58]=[O:59])=[CH:55][CH:54]=1>>[CH3:1][N:2]1[C:6]([C:53]2[S:57][C:56]([CH:58]=[O:59])=[CH:55][CH:54]=2)=[CH:5][CH:4]=[C:3]1[C:20]1[CH:21]=[C:22]2[C:30](=[CH:31][CH:32]=1)[N:29]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:28]1[CH:27]=[CH:26][C:25]([N:39]([C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[CH:24][C:23]2=1

Participants

3

Reactant 2

HCID 784285-Bromothiophene-2-carbaldehydeHCID 57796690HCID 57796690, compound

Product 1

HCID 57796684HCID 57796684, compound

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-ec6ca7500af44396b027b8b3058fa4e2
Source dataset
uspto-grants-2009_08
Patent number
US07569704B1

Reaction notes

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