5-Formyl-2-thiopheneboronic acid → HCID 86641779, compound

HRID 221163Notes

Reaction equation

HRID 221163 reaction equation
Br[C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([N:23]([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][CH3:27])=[CH:10][C:11]=3[C:12]2([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH2:17][CH3:18])=[CH:4][CH:3]=1.[CH:32]([C:34]1[S:38][C:37](B(O)O)=[CH:36][CH:35]=1)=[O:33]>>[CH2:19]([C:12]1([CH2:15][CH2:16][CH2:17][CH3:18])[C:13]2[CH:14]=[C:2]([C:37]3[S:38][C:34]([CH:32]=[O:33])=[CH:35][CH:36]=3)[CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][C:9]([N:23]([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][CH3:27])=[CH:8][CH:7]=2)[CH2:20][CH2:21][CH3:22]

Participants

3

Reactant 2

HCID 27734305-Formyl-2-thiopheneboronic acidHCID 58239559(7-bromo-9,9-dibutyl-9H-fluoren-2-yl)-dibutylamine

Product 1

HCID 86641779HCID 86641779, compound

Procedure

As shown in Scheme 2, 7-bromo-9H-fluoren-2-ylamine is reacted with 1-iodobutane to form (7-bromo-9,9-dibutyl-9H-fluoren-2-yl)-dibutylamine (21). Then, (7-bromo-9,9-dibutyl-9H-fluoren-2-yl)-dibutylamine (21) is reacted with 5-formyl-2-thiopheneboronic acid by Suzuki coupling reaction to obtain 5-(9,9-Dibutyl-7-dibutylamino-9H-fluoren-2-yl)-thiophene-2-carbaldehyde (22a). Finally, in acetonitrile, 5-(9,9-Dibutyl-7-dibutylamino-9H-fluoren-2-yl)-thiophene-2-carbaldehyde (22a) is reacted with cyanoacetic acid by using piperidine as a catalyst, to obtain 2-Cyano-3-[5-(9,9-dibutyl-7-dibutylamino-9H-fluoren-2-yl)-thiophen-2-yl]-acrylic acid (23a).

Sources & evidence

ORD record
ord-ed18a9fb90b748e6b4ffd28e78b67a13
Source dataset
uspto-grants-2012_06
Patent number
US08203068B2

Reaction notes

Loading…