Dimethylformamide → HCID 86623738、化合物

HRID 1173472ノート

反応式

HRID 1173472 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:12][C:13]([F:16])([F:15])[F:14])[CH2:9][CH2:10][OH:11])=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1.[NH4+].[OH-].[CH3:23][N:24](C=O)C>[C-]#N.[C-]#N.[Zn+2].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>[OH:11][CH2:10][CH2:9][N:8]([CH2:12][C:13]([F:16])([F:15])[F:14])[C:5]1[CH:6]=[CH:7][C:2]([C:23]#[N:24])=[CH:3][C:4]=1[C:17]([F:20])([F:19])[F:18]

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 59557180HCID 59557180、化合物

生成物 1

HCID 86623738HCID 86623738、化合物

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
80 °C

実験手順

A mixture of 2-[[4-bromo-2-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]ethanol (0.699 g, 1.92 mmol) and Zn(CN)2 (0.157 g, 1.34 mmol) in DMF (5 mL) was sparged with N2 for 15 min at rt and Pd(PPh3)4 (0.111 g, 0.096 mmol) was added in one portion, taking care not to allow air into the reaction flask. The mixture was heated to 80° C. under N2 for 40 min, cooled, poured into dilute NH4OH, and the whole was extracted with Et2O (×3). The combined organic portions were washed (water, brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.571 g of the title compound as a colorless gum: 1H NMR (300 MHz, CDCl3) δ 7.97 (d, J=1.6 Hz, 1H), 7.82 (dd, J=8.4, 1.8 Hz, 1H), 7.56 (d, J=8.6 Hz, 1H), 3.86 (q, J=8.9 Hz, 2H), 3.69 (t, J=2H), 3.50 (t, J=5.2 Hz, 2H), 1.74 (bs, 1H).

後処理

  1. customwas sparged with N2 for 15 min at rt
  2. temperaturecooled
  3. extractionthe whole was extracted with Et2O (×3)
  4. washThe combined organic portions were washed (water, brine)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (EtOAc/hexanes)

出典と根拠

ORDレコード
ord-d235162abdf843c2b238924e170e4826
出典データセット
uspto-grants-2010_11
特許番号
US07834063B2

反応ノート

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