Water → HCID 59729914、化合物

HRID 130720

反応式

HRID 130720 の反応式
[C:1]([O:5][C:6](=[O:24])[N:7]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[Cl:31][C:32]1[CH:39]=[C:38](F)[CH:37]=[CH:36][C:33]=1[C:34]#[N:35].O>CN(C=O)C>[C:1]([O:5][C:6](=[O:24])[N:7]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:38]2[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[C:32]([Cl:31])[CH:39]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1090002-Chloro-4-fluorobenzonitrileHCID 59717863HCID 59717863、化合物

生成物 1

HCID 59729914HCID 59729914、化合物収率 95.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Combine the compound from Example 218 step 2 (692 mg, 2.12 mmol) and K2CO3 (323 mg, 2.33 mmol) in DMF (9 mL), stir the mixture at room temperature for 30 min and then add 2-chloro-4-fluoro-benzonitrile (330 mg, 2.12 mmol), and heat at 100° C. overnight. Cool to ambient temperature and pour into water. Extract the aqueous layer with EtOAc. Dry the organic layer over Na2SO4 and eliminate the solvent. Purify by flash chromatography on silica gel (eluent: EtOAc/hexane 15/85) to obtain the title compound (940 mg, 95%). Electrospray MS M−1 ion=461, 1H-NMR (CDCl3, 400 MHz): 7.57 (d, 1H, J=7.8 Hz), 7.36-7.13 (m, 7H), 7.00-6.85 (m, 4H), 4.44-4.36 (m, 2H), 3.49-3.32 (m, 2H), 2.83-2.73 (m, 2H), 1.51-1.43 (m, 9H).

後処理

  1. extractionExtract the aqueous layer with EtOAc
  2. dry with materialDry the organic layer over Na2SO4
  3. customPurify by flash chromatography on silica gel (eluent: EtOAc/hexane 15/85)

出典と根拠

ORDレコード
ord-38316bf226df4a66a0471a9188d7be9a
出典データセット
uspto-grants-2008_06
特許番号
US07381719B2

関連ノート

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