1,2-Dibromoethane → 1,3-dichloro-8,8-dimethyl-5,6-dihydro-8H-7-oxa-2,4,4b-triaza-fluorene

HRID 334177ノート

反応式

HRID 334177 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:8][CH2:9]Br.[Cl:11][C:12]1[N:13]=[C:14]([Cl:25])[C:15]2[CH:20]=[C:19]([C:21]([OH:24])([CH3:23])[CH3:22])[NH:18][C:16]=2[N:17]=1>CN(C=O)C>[Cl:25][C:14]1[C:15]2[CH:20]=[C:19]3[N:18]([CH2:8][CH2:9][O:24][C:21]3([CH3:22])[CH3:23])[C:16]=2[N:17]=[C:12]([Cl:11])[N:13]=1

参加物

5

反応物 3

HCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 866673872-(2,4-Dichloro-7h-pyrrolo[2,3-d]pyrimidin-6-yl)propan-2-ol

生成物 1

HCID 866673881,3-dichloro-8,8-dimethyl-5,6-dihydro-8H-7-oxa-2,4,4b-triaza-fluorene

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

Cesium carbonate (1.2 g, 3.7 mmol) and 1,2-dibromoethane (316 μL, 3.7 mmol) were added to a solution of 2-(2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-propan-2-ol (304 mg, 1.23 mmol) in DMF (4 mL) and the reaction mixture was heated at 100° C. for 45 min, then partitioned between water and ethyl acetate. The organic extract was separated and washed with brine, then dried (Na2SO4) and concentrated in vacuo affording 1,3-dichloro-8,8-dimethyl-5,6-dihydro-8H-7-oxa-2,4,4b-triaza-fluorene. A mixture of 1,3-dichloro-8,8-dimethyl-5,6-dihydro-8H-7-oxa-2,4,4b-triaza-fluorene (1.23 mmol), morpholine (236 μL, 2.69 mmol) and triethylamine (342 μL, 2.46 mmol) in IMS (3 mL) was heated at reflux for 3 h, then concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, gradient 0 to 40% ethyl acetate in cyclohexane) affording 3-Chloro-8,8-dimethyl-1-morpholin-4-yl-5,6-dihydro-8H-7-oxa-2,4,4b-triaza-fluorene (159 mg, 40%). LCMS (method A): RT=3.13 min, [M+H]+=323.

後処理

  1. custompartitioned between water and ethyl acetate
  2. extractionThe organic extract
  3. customwas separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a407c22891bd46939b8874ec8cd99424
出典データセット
uspto-grants-2014_11
特許番号
US08883799B2

反応ノート

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