Phenylsilane → 5-Phenyl-3-(tetrahydro-thiopyran-4-ylamino)-thiophene-2-carboxylic acid methyl ester

HRID 749381

반응식

HRID 749381 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH2:10])=[O:4].[S:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1.C1([SiH3])C=CC=CC=1>C1COCC1.[Sn](CCCC)(CCCC)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH:10][CH:20]1[CH2:21][CH2:22][S:17][CH2:18][CH2:19]1)=[O:4]

참가 물질

6

반응물 3

HCID 12752PhenylsilaneHCID 66173Tetrahydrothiopyran-4-oneHCID 700562Methyl 3-amino-5-phenylthiophene-2-carboxylate

생성물 1

HCID 597523745-Phenyl-3-(tetrahydro-thiopyran-4-ylamino)-thiophene-2-carboxylic acid methyl ester수율 56.5%

시약·촉매·용매 2

HCID 12688Dibutyltin dichloride촉매HCID 8028Tetrahydrofuran용매

실험 절차

Reductive amination of 3-amino-5-phenyl-thiophene-2-carboxylic acid methyl ester (0.933 g, 4.0 mmol) and tetrahydro-thiopyran-4-one (0.464 g, 4.0 mmol)in THF (1.0 mL) employing Bu2SnCl2 (60.5 mg, 0.2 mmol) and PhSiH3 (0.476 g, 0.542 mL) was carried out as described for example 13, step 1 gave 5-phenyl-3-(tetrahydro-thiopyran-4-ylamino)-thiophene-2-carboxylic acid methyl ester (0.753 g, 56.3%). NMR 1H (CDCl3, 400 MHz): 7.64-7.6 (m, 2H), 7.44-7.34 (m, 3H), 6.9 (brm, 1H), 6.81 (brs, 1H), 3.84 (s, 3H), 3.5-3.4 (m, 1H), 2.85-2.7 (m, 4H), 2.4-2.25 (m, 2H), 1.85-1.7 (m, 2H).

출처 및 근거

ORD 기록
ord-1028fcfb22304808ab6ba1b22f3223a0
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402608B2

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