Ethanol → HCID 69586461, 화합물

HRID 723049노트

반응식

HRID 723049 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([NH2:20])=[C:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15](Br)[CH:14]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4].[C:21]1([CH3:36])[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1C1C=CC=CC=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].C(O)C>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.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([NH2:20])=[C:8]([S:10]([C:13]2[CH:14]=[C:15]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH3:36])[CH:16]=[CH:17][CH:18]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4]

참가 물질

7

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 15887404(2'-Methyl-[1,1'-biphenyl]-2-yl)boronic acidHCID 695864675-Amino-4-(3-bromo-benzenesulfonyl)-thiophene-2-carboxylic acid methyl ester

생성물 1

HCID 69586461HCID 69586461, 화합물

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

5-Amino-4-(2′-methyl-biphenyl-3-sulfonyl)-thiophene-2-carboxylic acid methyl ester was prepared following the procedure as in Example 1: step c using 5-amino-4-(3-bromo-benzenesulfonyl)-thiophene-2-carboxylic acid methyl ester (598.9 mg, 1.6 mmol) (Example 20: steps a–c), o-tolyl-phenyl boronic acid (435.6 mg, 3.2 mmol), Pd(PPh3)4 (366.6 mg, 0.32 mmol), aqueous Na2CO3 (2M, 6.4 mL, 12.8 mmol), ethanol (6.4 mL) and toluene (12.8 mL). Purification by flash column chromatography (Biotage Flash™ System—40 M SiO2 column) (25% EtOAc in hexanes) of the residue yielded the adduct (137 mg, 23%) as a light brown solid. ESI-MS (m/z): Calcd. for C19H17NO4S2: 387.02; found: 388.3. 5-Amino-4-(2′-methyl-biphenyl-3-sulfonyl)-thiophene-2-carboxylic acid methyl ester (61 mg, 16 mmol) was then converted to the amidine and purified as described in Example 20: step f to isolate the title compound (6 mg, 10%) as a light brown solid. 1H-NMR (CD3OD): δ: 7.96–7.99 (m, 1H), 7.95 (s, 1H), 7.93–7.94 (m, 1H), 7.63–7.69(m, 3H), 7.18–7.32 (m, 3H), 2.22 (s, 3H). ESI-MS (m/z): Calcd. for C18H17N3O2S2: 372.0 (M+H); found: 372.2.

후처리

  1. customPurification by flash column chromatography (Biotage Flash™ System—40 M SiO2 column) (25% EtOAc in hexanes) of the residue

출처 및 근거

ORD 기록
ord-195814ce04cd4726a37c78d64ec0118a
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138530B2

반응 노트

불러오는 중…