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N,N,N',N'-Tetramethylethylenediamine → HCID 56848134、化合物

HRID 2093727
ノート
印刷プレビュー

反応式

HRID 2093727 の反応式
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:26])=[C:7]([C:15]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[O:16])[C:8]([CH:12]3[CH2:14][CH2:13]3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:27][N:28](CCN(C)C)C.CCOC(C)=O.C1CCCCC1>CN(C=O)C.[C-]#N.[Zn+2].[C-]#N.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].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[C:27]([C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:26])=[C:7]([C:15]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[O:16])[C:8]([CH:12]3[CH2:13][CH2:14]3)=[N:9]2)=[CH:4][CH:3]=1)#[N:28]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 21867204Cyclohexane ethylacetateHCID 568480807-Bromo-2-cyclopropyl-N-[(4-fluorophenyl)-methyl]-4-methyl-quinoline-3-carboxylic acid amide

生成物 1

HCID 56848134HCID 56848134、化合物収率 191.5%

試薬・触媒・溶媒 4

HCID 11186Zinc cyanide (Zn(CN)2)触媒
HCID 636044
1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
触媒
HCID 9811564Bis(dibenzylideneacetone)palladium触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
160 °C

実験手順

To a solution of 880 mg (2.13 mmol) 7-Bromo-2-cyclopropyl-N-[(4-fluorophenyl)-methyl]-4-methyl-quinoline-3-carboxylic acid amide (example 28) in DMF (3 mL) were added 70 μL (0.47 mmol) TMEDA, 152 mg (1.28 mmol) Zinccyanide, 4 mg (0.007 mmol) Pd2 dba3 and 25 mg (0.040 mmol) Xantphos. The reaction solution was degasses and flushed with nitrogen three times and then heated in MW to 160° C. for 4 min. After cooling to RT the mixture was filtered through celite and it was washed with dichloromethane. The combined organic layers were concentrated in vacuo. After CC (EtOAc/cyclohexane 1:2) of the residue, 325 mg (0.90 mmol, 42%) 7-Cyano-2-cyclopropyl-N-[(4-fluorophenyl)-methyl]-4-methyl-quinoline-3-carboxylic acid amide (example 38) were obtained. MS: m/z 360.1 [M+H]+.

後処理

  1. customflushed with nitrogen three times
  2. temperatureAfter cooling to RT the mixture
  3. filtrationwas filtered through celite and it
  4. washwas washed with dichloromethane
  5. concentrationThe combined organic layers were concentrated in vacuo

出典と根拠

ORDレコード
ord-78188a9e4d9f41d0b380faacf1ed9dde
出典データセット
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08445512B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート