Sodium Carbonate → 5-Trimethylsilylethynyl-2,3-bis-(2-methyl-3-benzo[3,2-b]thienyl)thiophene

HRID 426430

반응식

HRID 426430 반응식
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].[CH3:7][C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]=1[C:17]1[S:18][CH:19]=[CH:20][C:21]=1[C:22]1[C:23]2[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=2[S:25][C:26]=1[CH3:27].[CH3:32][C:33]1SC2C=CC=CC=2C=1B(O)O.BrC1SC=CC=1Br.C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>[Pd].ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1.O>[CH3:1][Si:2]([C:5]#[C:6][C:19]1[S:18][C:17]([C:9]2[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[S:12][C:8]=2[CH3:7])=[C:21]([C:22]2[C:23]3[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=3[S:25][C:26]=2[CH3:27])[CH:20]=1)([CH3:4])[CH3:3].[C:32]([C:20]1[C:21]([C:22]2[C:23]3[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=3[S:25][C:26]=2[CH3:27])=[C:17]([C:9]2[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[S:12][C:8]=2[CH3:7])[S:18][CH:19]=1)#[CH:33]

참가 물질

13

반응물 6

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 66111TrimethylsilylacetyleneHCID 765902,3-DibromothiopheneHCID 58933004(2-Methyl-1-benzothiophen-3-yl)boronic acidHCID 667041632,3-Bis(2-methylbenzothiophen-3-yl)thiophene

생성물 2

HCID 667043115-Trimethylsilylethynyl-2,3-bis-(2-methyl-3-benzo[3,2-b]thienyl)thiopheneHCID 87118226Ethynyl-2,3-bis-(2-methyl-3-benzo[3,2-b]thienyl)thiophene

시약·촉매·용매 5

HCID 23938Palladium촉매HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

5-Trimethylsilylethynyl-2,3-bis-(2-methyl-3-benzo[3,2-b]thienyl)thiophene is synthesized by the Sonogashira coupling reaction of trimethylsilylacetylene and the bromo-derivative of 2,3-bis-(2-methyl-3-benzo[3,2-b]thienyl)thiophene, which is also prepared from the Suzuki cross-coupling reaction of 2.5 equivalents of 2-methyl-3-benzo[3,2-b]thienylboronic acid and 2,3-dibromothiophene in the presence of the palladium catalyst, Pd(PPh3)4, and sodium carbonate in a heterogeneous mixture of water and THF according to the procedure similar to that of (L1). Subsequent deprotection of the trimethylsilyl group using potassium carbonate in dichloromethane solution gives the target ligand ethynyl-2,3-bis-(2-methyl-3-benzo[3,2-b]thienyl)thiophene (L5). The synthetic route is shown in FIG. 12. Excitation of the ligand with λ≦352 nm light resulted in the formation of the close form, corresponding to the photocyclization product.

출처 및 근거

ORD 기록
ord-a5694d3d684a47aaa9adec4d64fca1ec
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08107150B2

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