Dimethylformamide → HCID 45139208、化合物

HRID 1949118ノート

反応式

HRID 1949118 の反応式
Br[C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([F:15])[CH:12]=3)[NH:7][C:6]=2[C:5]([O:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])=[C:4]2[NH:22][C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][C:28]=3[C:3]=12.[CH3:30][N:31](C=O)C>[C-]#N.[Zn+2].[C-]#N.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>[CH3:20][N:19]([CH3:21])[CH2:18][CH2:17][O:16][C:5]1[C:6]2[NH:7][C:8]3[C:13](=[CH:12][C:11]([F:15])=[CH:10][CH:9]=3)[C:14]=2[C:2]([C:30]#[N:31])=[C:3]2[C:28]3[CH:27]=[C:26]([F:29])[CH:25]=[CH:24][C:23]=3[NH:22][C:4]=12

参加物

5

反応物 2

HCID 6228DimethylformamideHCID 59238889HCID 59238889、化合物

生成物 1

HCID 45139208HCID 45139208、化合物収率 46%

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
160 °C

実験手順

A mixture of 2-(12-bromo-2,10-difluoro-5,7-dihydroindolo[2,3-b]carbazol-6-yloxy)-N,N-dimethylethanamine (97.8 mg, 0.1991 mmol), zinc cyanide (233.7 mg, 1.9910 mmol) and tetrakis(triphenylphosphine)palladium (0) (23.0 mg, 0.01991 mmol) in anhydrous DMF was purged with high-purity Ar for five minutes, sealed with Teflon cap and heated to 160° C. for 12 hours. The reaction mixture was cooled down and filtered. The solvent was removed via vacuum pump. The residue was purified via flash chromatography to provide the title compound (37.3 mg, 46%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.90 (s, 2 H), 8.39 (dd, J=10.2, 2.8 Hz, 2 H), 7.55 (dd, 8.8, 4.4 Hz, 2 H), 7.31 (td, J=8.8, 2.4 Hz, 2 H), 4.33 (t, J=4.2 Hz, 2 H), 2.74 (t, J=4.2 Hz, 2 H), 2.35 (s, 6 H); MS (ESI) m/z 403.1 (M−H)−; MS (ESI) m/z 405.0 (M+H)+

後処理

  1. customwas purged with high-purity Ar for five minutes
  2. customsealed with Teflon
  3. customcap
  4. temperatureThe reaction mixture was cooled down
  5. filtrationfiltered
  6. customThe solvent was removed via vacuum pump
  7. customThe residue was purified via flash chromatography

出典と根拠

ORDレコード
ord-264d08095b3a471f9053c070069cd06c
出典データセット
uspto-grants-2013_03
特許番号
US08399502B2

反応ノート

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