Butyl iodide → (7-bromo-9H-fluoren-2-yl)-dibutyl amine

HRID 1965871Notes

Reaction equation

[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([NH2:15])=[CH:10][C:11]=3[CH2:12]2)=[CH:4][CH:3]=1.I[CH2:17][CH2:18][CH2:19][CH3:20]>>[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([N:15]([CH2:14][CH2:2][CH2:3][CH3:4])[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][C:11]=3[CH2:12]2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 10962Butyl iodide

HCID 231262-Amino-7-bromofluorene

Product 1

HCID 59325934(7-bromo-9H-fluoren-2-yl)-dibutyl amine

Procedure

As shown in Scheme 1, 7-bromo-9H-fluoren-2-ylamine is reacted with 1-iodobutane to form (7-bromo-9H-fluoren-2-yl)-dibutyl amine (11). Then, (7-bromo-9H-fluoren-2-yl)-dibutyl amine (11) is reacted with 5-formyl-2-thiopheneboronic acid by Suzuki coupling reaction to obtain 5-(7-dibutylamino-9H-fluoren-2-yl)-thiophene-2-carbaldehyde (12a). Finally, in acetonitrile, 5-(7-dibutylamino-9H-fluoren-2-yl)-thiophene-2-carbaldehyde (12a) is reacted with cyanoacetic acid by using piperidine as a catalyst, to obtain 2-cyano-3-[5-(7-dibutylamino-9H-fluoren-2-yl)-thiophen-2-yl]-acrylic acid (13a).

Sources & evidence

ORD record: ord-aa34c5d96c2f4ab996149e02d485a87c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08419808B2

Reaction notes

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