Aniline → HCID 178420468、化合物

HRID 45922

反応式

HRID 45922 の反応式
Br[C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][NH:8][C:4]=2[CH:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1COCC1>[C:12]1([NH:11][C:2]2[CH:10]=[CH:9][C:5]3[NH:6][CH:7]=[N:8][C:4]=3[CH:3]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

6

反応物 3

HCID 6115AnilineHCID 7852996-Bromo-1H-benzimidazoleHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 178420468HCID 178420468、化合物

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

The compound was synthesized starting from 5-bromobenzimidazole (1.0 g; 5 mmol; 1 eq.), aniline (559 mg; 0.547 ml; 6 mmol; 1.2 eq.), lithiumbis(trimethylsilyl)amide 1M in THF (11 ml; 11 mmol; 2.2 eq.), 2-dicyclohexylphos-phino-2″-(N,N-dimethylamino)biphenyl) (45 mg; 0.12 mmol; 0.024 eq.; 2.4 mol %), Pd2 dba3 (45 mg; 0.05 mmol; 0.01 eq.; 1 mol %) and THF (5 ml) according to method 1; Yield: 0.565 g (54.1%); MS m/z: 210.2 [M+H]+; 1H-NMR (500 MHz, DMSO d6): δ 6.72-6.75 (m, 1H); 6.94-6.96 (m, 1H); 7.00-7.02 (m, 2H); 7.16-7.19 (m, 2H); 7.25 (br s, 1H); 7.47 (d, 1H, 3J=8.5 Hz); 7.98 (br s, 1H); 8.04 (s, 1H); 12.13 (br s, 1H); HPLC (METHOD [A]): rt 10.62 min (87.0%)

後処理

  1. customThe compound was synthesized
  2. customrt 10.62 min (87.0%)

出典と根拠

ORDレコード
ord-2ae5875145124ebb98f59a6330822fb6
出典データセット
uspto-grants-2013_09
特許番号
US08541596B2

関連ノート

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