tert-Butanol → (4-Bromo-6-methoxy-quinolin-3-yl)-carbamic acid tert-butyl ester

HRID 639002ノート

反応式

HRID 639002 の反応式
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1C(O)=O.C([N:19]([CH2:22]C)CC)C.[C:24]([OH:28])([CH3:27])([CH3:26])[CH3:25].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:36])C=CC=CC=1>CN(C=O)C>[C:24]([O:28][C:22](=[O:36])[NH:19][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[Br:1])=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)([CH3:27])([CH3:26])[CH3:25]

参加物

6

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 684531854-Bromo-6-methoxyquinoline-3-carboxylic acid

生成物 1

HCID 68455075(4-Bromo-6-methoxy-quinolin-3-yl)-carbamic acid tert-butyl ester収率 53%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 4-Bromo-6-methoxyquinoline-3-carboxylic acid (34 g, 0.121 mole), triethylamine (141 mL) and tert-butanol (181 mL) in dry DMF (400 mL) was added diphenylphosphoryl azide (36.6 g, 28.6 mL, 0.133 mole). The mixture was heated at 100° C. for 1 h (see Note), then cooled and concentrated. The residue was dissolved in CH2Cl2 and washed with water (some insoluble material was removed by filtration). The aqueous phase was extracted with dichloromethane and the combined organics were dried (Na2SO4) and concentrated. Chromatography on silica gel (1 kg, 1:1 ether/light petroleum ether) gave the carbamate (22.7 g, 53%): MS (ES) m/e 309/311 (M+H)+, 354/6.

後処理

  1. temperaturecooled
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with water (some insoluble material
  5. customwas removed by filtration)
  6. extractionThe aqueous phase was extracted with dichloromethane
  7. dry with materialthe combined organics were dried (Na2SO4)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-4e8225d3571e4c5895503a9029fec8a2
出典データセット
uspto-grants-2010_04
特許番号
US07691850B2

反応ノート

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