Hydrochloric Acid → 4-[(2-Ethylquinolin-4-yloxy)methyl]phenylboronic acid hydrochloride

HRID 487417

反応式

HRID 487417 の反応式
[CH2:1]([C:3]1[CH2:12][C:11](=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2].[H-].[Na+].Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([B:24]2[O:29]CC(C)(C)C[O:25]2)=[CH:20][CH:19]=1.CC1C=CC(B(O)O)=CC=1.CC(C)(CO)CO.BrN1C(=O)CCC1=O.[ClH:57]>CN1C(=O)CCC1.C1CCCCC1.C(OCC)(=O)C.N(C(C)(C)C#N)=NC(C)(C)C#N.O>[ClH:57].[CH2:1]([C:3]1[CH:12]=[C:11]([O:13][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([B:24]([OH:29])[OH:25])=[CH:20][CH:19]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2]

参加物

13

反応物 7

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 31344Neopentyl glycolHCID 67184N-bromobutanimideHCID 79799Tolylboronic acidHCID 110005212-(4-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinaneHCID 150208512-ethyl-3H-quinolin-4-one

生成物 1

HCID 677828274-[(2-Ethylquinolin-4-yloxy)methyl]phenylboronic acid hydrochloride

試薬・触媒・溶媒 5

HCID 6547Azobisisobutyronitrile触媒HCID 962Water溶媒2 回HCID 8078Cyclohexane溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒2 回

実験手順

A solution of 2-ethyl-4-quinolone (6.9 g; 0.04 mole) in (NMP) (50 ml) was added over 30 minutes to a stirred suspension of sodium hydride (1.6 g of a 60% dispersion in mineral oil; 0.04 mole) in NMP (50 ml) and the mixture stirred for 30 minutes. A solution of 2-(4-bromomethylphenyl)-5,5-dimethyl-1,3,2-dioxaborinane in cyclohexane [previously prepared by heating a mixture of 4-methylphenylboronic acid (6.8 g) and 2,2-dimethylpropan-1,3-diol (5.2 g) in cyclohexane (150 ml) at reflux with azeotropic removal of water, followed by the addition of N-bromosuccinimide (8.9 g) and azo(bisisobutyronitrile) (0.2 g), heating the mixture at reflux for 3 hours, and removing suspended succinimide by filtration] was added and the mixture was heated at 60°-70°]C. for 18 hours. The mixture was allowed to cool and acetic acid was then added until the mixture was at pH 4, followed by water (200 ml) and ethyl acetate (200 ml). The mixture was stirred for 20 minutes and then the organic phase was separated, washed with water and dried (MgSO4). Volatile material was removed by evaporation to give a crystalline solid. The solid was dissolved in ethyl acetate (150 ml), concentrated hydrochloric acid (3 ml) and water (3 ml) were added and the mixture was stirred for 18 hours. The resultant precipitate was collected by filtration, washed with ethyl acetate and dried to give 4-[(2-ethylquinolin-4-yloxy)methyl]phenylboronic acid hydrochloride (7 g) as a solid; NMR similar to that of compound G of Procedure B, step (ii).

後処理

  1. temperatureby heating
  2. temperatureheating the mixture
  3. temperatureat reflux for 3 hours
  4. customremoving
  5. filtrationby filtration]
  6. additionwas added
  7. temperaturethe mixture was heated at 60°-70°]C
  8. temperatureto cool
  9. additionacetic acid was then added until the mixture
  10. customthe organic phase was separated
  11. washwashed with water
  12. dry with materialdried (MgSO4)
  13. customVolatile material was removed by evaporation
  14. customto give a crystalline solid
  15. stirringthe mixture was stirred for 18 hours
  16. filtrationThe resultant precipitate was collected by filtration
  17. washwashed with ethyl acetate
  18. customdried

出典と根拠

ORDレコード
ord-a1c57121e52042dba3153cbd54bf96dc
出典データセット
uspto-grants-1994_03
特許番号
US05294716

関連ノート

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