4-Bromobenzaldehyde → 4-(5-(4-(diphenylamino)phenyl)-1-methyl-1H-pyrrol-2-yl)benzaldehyde

HRID 2099953Notes

Reaction equation

HRID 2099953 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.BrC1C=CC(N(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:30][N:31]1[C:35]([Sn](CCCC)(CCCC)CCCC)=[CH:34][CH:33]=[C:32]1[C:49]1[CH:67]=[CH:66][C:52]([N:53]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)=[CH:51][CH:50]=1.CN1C=CC=C1[Sn](CCCC)(CCCC)CCCC>>[C:54]1([N:53]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[C:52]2[CH:66]=[CH:67][C:49]([C:32]3[N:31]([CH3:30])[C:35]([C:2]4[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=4)=[CH:34][CH:33]=3)=[CH:50][CH:51]=2)[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1

Participants

5

Reactant 4

HCID 707414-BromobenzaldehydeHCID 6428384-BromotriphenylamineHCID 27693971-methyl-2-(tributylstannyl)-1H-pyrroleHCID 577966924-(1-methyl-5-(tributylstannyl)-1H-pyrrole-2-yl)-N,N-diphenylaniline2×

Product 1

HCID 867609284-(5-(4-(diphenylamino)phenyl)-1-methyl-1H-pyrrol-2-yl)benzaldehyde

Procedure

The compound of the present example was synthesized by the same method as described in example 1, except that 1.85 parts of 4-bromo-benzaldehyde was used to substitute 4-bromo-N,N-diphenylaniline, and 6.63 parts of 4-(1-methyl-5-(tributylstannyl)-1H-pyrrole-2-yl)-N,N-diphenylaniline (13) was used to substitute 1-methyl-2-(tributylstannyl)-1H-pyrrole, wherein 4-(1-methyl-5-(tributylstannyl)-1H-pyrrole-2-yl)-N,N-diphenylaniline (13) was synthesized according to the method illustrated in Armaroli, N.; Balzani, V. Angew. Chem. Int. Ed. 2007, 46, 52.

Workup

  1. customwas synthesized

Sources & evidence

ORD record
ord-4b5587d14dbc4243b9bf643705ae9272
Source dataset
uspto-grants-2009_08
Patent number
US07569704B1

Reaction notes

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