反応式
ClC1C=CC=CC=1[C:8]1[CH:12]=[CH:11][S:10][C:9]=1[C:13]([NH:15][C:16]1[CH:21]=[C:20]([C:22](=[O:27])[NH:23][CH:24]2[CH2:26][CH2:25]2)[CH:19]=[CH:18][C:17]=1[CH3:28])=[O:14].[B:29]1(B2OC(C)(C)C(C)(C)O2)[O:33]C(C)(C)C(C)(C)[O:30]1.CC([O-])=O.[K+]>CN(C=O)C>[CH:24]1([NH:23][C:22]([C:20]2[CH:19]=[CH:18][C:17]([CH3:28])=[C:16]([NH:15][C:13]([C:9]3[S:10][C:11]([B:29]([OH:33])[OH:30])=[CH:12][CH:8]=3)=[O:14])[CH:21]=2)=[O:27])[CH2:26][CH2:25]1参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 90 °C
実験手順
A solution of 1.0 g (2.64 mmol) of 5-bromo-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)thiophene-2-carboxamide (Example 136, Step B), bis(pinacolato)diborane (1.0 g, 3.95 mmol) and KOAc (1.30 g, 13.2 mmol) in DMF (15 mL) was purged with argon and Pd(dppf)2Cl2/CH2Cl2 complex (65 mg, 0.08 mmol) was added followed by heating at 90° C. for 16 h. After cooling to rt, the mixture was partitioned between EtOAc (250 mL) and water (50 mL) and the layers were separated. The organic portion was washed with additional water, then brine, then dried over anhyd Na2SO4, filtered, and concentrated under vacuum to afford 1.62 g of a brown semi-solid as the crude product mixture. This material was triturated with EtOAc and filtered to afford 626 mg of the compound a containing ˜10% of the boronate ester. This material was used as is without any further purification. HPLC Ret time=2.36 min. LCMS [M+H]+ 345.2.
後処理
- additionwas added
- temperatureAfter cooling to rt
- customthe mixture was partitioned between EtOAc (250 mL) and water (50 mL)
- customthe layers were separated
- washThe organic portion was washed with additional water
- dry with materialbrine, then dried over anhyd Na2SO4
- filtrationfiltered
- concentrationconcentrated under vacuum
出典と根拠
- ORDレコード
- ord-135ecc26917e4d76af946caa32bbb78a
- 出典データセット
- uspto-grants-2011_05
- 特許番号
- US07935696B2
関連ノート
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