Toluene → 5-(7-dibutylamino-9H-fluoren-2-yl)-thiophene-2-carbaldehyde

HRID 1965883Notes

Reaction equation

Br[C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([N:15]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:10][C:11]=3[CH2:12]2)=[CH:4][CH:3]=1.[CH:24]([C:26]1[S:30][C:29](B(O)O)=[CH:28][CH:27]=1)=[O:25].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CO>[CH2:16]([N:15]([CH2:20][CH2:21][CH2:22][CH3:23])[C:9]1[CH:10]=[C:11]2[C:6]([C:5]3[CH:4]=[CH:3][C:2]([C:29]4[S:30][C:26]([CH:24]=[O:25])=[CH:27][CH:28]=4)=[CH:14][C:13]=3[CH2:12]2)=[CH:7][CH:8]=1)[CH2:17][CH2:18][CH3:19]

Participants

Conditions

Temperature: 60 °C

Procedure

Under N2 atmosphere, 0.37 parts of (7-bromo-9H-fluoren-2-yl)-dibutyl amine (11), 0.19 parts of 5-formyl-2-thiopheneboronic acid, 0.41 parts of potassium carbonate, and 0.16 parts of PdCl2(dppf) were added into 5 parts of toluene and 5 parts of CH3OH, followed by stirring and mixing. Then, the reaction mixture was heated to 60° C. and reacted for 18 hours. After the reaction mixture was quenched by water, using the diethyl ether to extract the product, and magnesium sulfate was used for dehydration. After removing the solvent, the residual was purified with chromatography method column by using dichloromethane/hexane co-solvent as an eluent, to obtain a compound (12a) of the present example. This compound was in a form of a tangerine solid, and the yield of this compound was 61%.

Workup

additionmixing
customreacted for 18 hours
customAfter the reaction mixture was quenched by water
extractionto extract the product, and magnesium sulfate
customAfter removing the solvent
customthe residual was purified with chromatography method column

Sources & evidence

ORD record: ord-d74ca7c5d40c4def994e9e7e16f9f8c7
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08419808B2

Reaction notes

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