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

HRID 487417

반응식

HRID 487417 반응식
[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]

참가 물질

13

반응물 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

생성물 1

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

시약·촉매·용매 5

HCID 6547Azobisisobutyronitrile촉매HCID 962Water용매2회HCID 8078Cyclohexane용매2회HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a1c57121e52042dba3153cbd54bf96dc
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05294716

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