Sodium hydride → 1-(8-Bromo-quinolin-2-yl)-6,7-dihydro-1H-5,8-dioxa-1,3-diaza-cyclopenta[b]naphthalene

HRID 1745912ノート

反応式

HRID 1745912 の反応式
[NH:1]1[C:5]2=[CH:6][C:7]3[O:8][CH2:9][CH2:10][O:11][C:12]=3[CH:13]=[C:4]2[N:3]=[CH:2]1.[H-].[Na+].[Br:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:26]=1[N:25]=[C:24](Cl)[CH:23]=[CH:22]2>CN1CCCC1=O>[Br:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:26]=1[N:25]=[C:24]([N:1]1[C:5]3=[CH:6][C:7]4[O:8][CH2:9][CH2:10][O:11][C:12]=4[CH:13]=[C:4]3[N:3]=[CH:2]1)[CH:23]=[CH:22]2

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 109557558-Bromo-2-chloroquinolineHCID 222269786,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

生成物 1

HCID 222269031-(8-Bromo-quinolin-2-yl)-6,7-dihydro-1H-5,8-dioxa-1,3-diaza-cyclopenta[b]naphthalene収率 135%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
65 °C

実験手順

6,7-Dihydro-1H-5,8-dioxa-1,3-diaza-cyclopenta[b]naphthalene 81B (600 mg, 3,4 mMol) was dissolved in 15 mL of 1-methyl-2-pyrrolidinone under an atmosphere of dry N2. To this solution was added 60% sodium hydride in oil (136 mg, 3.40 mMol) and the reaction mixture was stirred for 15 minutes. 8-Bromo-2-chloro-quinoline 81A (750 mg, 3.10 mMol) was then added to the reaction mixture which was subsequently heated to 65° C. and reacted at this temperature overnight. The reaction mixture was then cooled to ambient temperature, partitioned between DCM and saturated aqueous NaHCO3, washed again with saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated under vacuum to give 1.60 g of an orange solid. The solid was chromatographed on flash silica gel eluting with a gradient from DCM to MeOH/DCM (0.5/99.5) to give 700 mg of the title compound 81C as a light yellow solid.

後処理

  1. customreacted at this temperature overnight
  2. temperatureThe reaction mixture was then cooled to ambient temperature
  3. custompartitioned between DCM and saturated aqueous NaHCO3
  4. washwashed again with saturated aqueous NaHCO3
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-84975314456948d1ab3ec1a0f26d990f
出典データセット
uspto-grants-2006_03
特許番号
US07019147B1

反応ノート

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