Methyl N-(triethylammoniosulfonyl)carbamate → 2-Chloro-4-methoxy-6-(4-trifluoromethyl-thiazol-2-yl)-pyridine

HRID 530755ノート

反応式

HRID 530755 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[S:9][CH2:10][C:11]([C:14]([F:17])([F:16])[F:15])(O)[N:12]=2)[CH:5]=[C:4]([O:18][CH3:19])[CH:3]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([O:18][CH3:19])[CH:5]=[C:6]([C:8]2[S:9][CH:10]=[C:11]([C:14]([F:17])([F:15])[F:16])[N:12]=2)[N:7]=1

参加物

4

反応物 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 866691152-(6-Chloro-4-methoxy-pyridin-2-yl)-4-trifluoromethyl-4,5-dihydro-thiazol-4-ol

生成物 1

HCID 866691142-Chloro-4-methoxy-6-(4-trifluoromethyl-thiazol-2-yl)-pyridine収率 48%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a solution of compound 20 (8.67 mmol) in THF (30 mL) was added Burgess Reagent (9.5 mmol). The reaction mixture was stirred at 60° C. for 30 min. The solution was concentrated in vacuo and H2O and DCM were added. The layers were separated and the organic layer was concentrated. The crude was purified by silica gel chromatography (eluent: petroleum ether/DCM 50 to 100%) to give compound 21 as a beige solid in 48% yield. MS (ESI, EI+): m/z=294.87 (MH+).

後処理

  1. concentrationThe solution was concentrated in vacuo and H2O and DCM
  2. additionwere added
  3. customThe layers were separated
  4. concentrationthe organic layer was concentrated
  5. customThe crude was purified by silica gel chromatography (eluent: petroleum ether/DCM 50 to 100%)

出典と根拠

ORDレコード
ord-035de6ad101646ddb373b359051a1b1a
出典データセット
uspto-grants-2016_05
特許番号
US09353100B2

反応ノート

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