Ethyl Acetate → N-(2-fluoroethyl)-4-(naphthalen-2-yl)thiazol-2-amine

HRID 1965838ノート

反応式

HRID 1965838 の反応式
Cl.[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]1[N:13]=[C:14]([NH2:17])[S:15][CH:16]=1.Br[CH2:19][CH2:20][F:21].C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CN1C(=O)CCC1>[F:21][CH2:20][CH2:19][NH:17][C:14]1[S:15][CH:16]=[C:12]([C:3]2[CH:4]=[CH:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:2]=2)[N:13]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 129822-Fluoroethyl bromideHCID 866409394-(Naphthalen-2-yl)thiazol-2-amine hydrochloride

生成物 1

HCID 59282917N-(2-fluoroethyl)-4-(naphthalen-2-yl)thiazol-2-amine収率 18%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

A mixture of 4-(naphthalen-2-yl)thiazol-2-amine hydrochloride (113 mg, 0.5 mmol), 1-bromo-2-fluoroethane (127 mg, 1 mmol), Cs2CO3 (326 mg, 1 mmol), and 15 mg KI in 2 mL of NMP was heated at 80 C for 20 min in a microwave reactor. After cooling to rt, the mixture was taken up to 50 mL EtOAc and washed with water (3×80 mL) and dried over MgSO4 and concentrated. The residue was chromatographed (hexane/EtOAc) to afford N-(2-fluoroethyl)-4-(naphthalen-2-yl)thiazol-2-amine as a white solid (10 mg, 18%). 1H NMR (400 MHz, CDCl3) δ 12.32 (s, 1 H), 8.29 (d, J=1.6 Hz, 1 H), 7.95-7.91 (m, 2 H), 7.86-7.83 (m, 1 H), 7.67 (dd, J=8.4, 2.0 Hz, 1 H), 7.57-7.54 (m, 2 H), 6.70 (s, 1 H), 4.79 (t, J=4.8 Hz, 1 H), 4.67 (t, J=4.8 Hz, 1 H), 3.71 (m, 1 H), 3.65 (m, 1 H); MS (ESI) m/z 273 (M+H+).

後処理

  1. temperaturewas heated at 80 C for 20 min in a microwave reactor
  2. washwashed with water (3×80 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed (hexane/EtOAc)

出典と根拠

ORDレコード
ord-d675f7f4a830417d8f736b09e237948e
出典データセット
uspto-grants-2013_04
特許番号
US08420052B2

反応ノート

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