Sodium Carbonate → (S)-4-(3,5-dichlorophenyl)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)quinoline-2-carbonitrile

HRID 2422547ノート

反応式

HRID 2422547 の反応式
[N+](C1C=CC(C([O:10][C@@:11]([C:18]2[N:19]=[N:20][N:21]([CH2:23][C:24]3[CH:33]=[C:32]4[C:27]([C:28](Cl)=[CH:29][C:30]([C:34]#[N:35])=[N:31]4)=[CH:26][CH:25]=3)[CH:22]=2)([C:14]([F:17])([F:16])[F:15])[CH2:12][CH3:13])=O)=CC=1)([O-])=O.[Cl:39][C:40]1[CH:41]=[C:42](B(O)O)[CH:43]=[C:44]([Cl:46])[CH:45]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:39][C:40]1[CH:41]=[C:42]([C:28]2[C:27]3[C:32](=[CH:33][C:24]([CH2:23][N:21]4[CH:22]=[C:18]([C@:11]([OH:10])([C:14]([F:16])([F:17])[F:15])[CH2:12][CH3:13])[N:19]=[N:20]4)=[CH:25][CH:26]=3)[N:31]=[C:30]([C:34]#[N:35])[CH:29]=2)[CH:43]=[C:44]([Cl:46])[CH:45]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 27343313,5-Dichlorophenylboronic acidHCID 66790930(S)-1-{1-[(4-chloro-2-cyanoquinolin-7-yl)methyl]-1H-1,2,3-triazol-4-yl}-1-(trifluoromethyl)propyl 4-nitrobenzoate

生成物 1

HCID 66790617(S)-4-(3,5-dichlorophenyl)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)quinoline-2-carbonitrile

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a solution of (S)-1-{1-[(4-chloro-2-cyanoquinolin-7-yl)methyl]-1H-1,2,3-triazol-4-yl}-1-(trifluoromethyl)propyl 4-nitrobenzoate (150 mg, 0.28 mmol) in DME (3 mL) was added tetrakis(triphenylphosphine)palladium (16 mg, 0.014 mmol), 3,5-dichlorophenylboronic acid (80 mg, 0.42 mmol) and aq. 2M Na2CO3 (0.42 mL, 0.84 mmol). After 1.5 h at 100° C., the reaction was quenched with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduce pressure. To this crude product was added THF (4 mL) and LiOH IM (1.4 mL, 1.4 mmol). After 2 h at rt, the reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduce pressure. Purification on silica gel (eluting with EtOAc/hexanes, 3:7) gave the title compound. MS (+ESI): 506 (M+H)+.

後処理

  1. customthe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionTo this crude product was added THF (4 mL) and LiOH IM (1.4 mL, 1.4 mmol)
  8. waitAfter 2 h at rt
  9. customthe reaction was quenched with saturated aqueous NH4Cl
  10. extractionextracted with EtOAc
  11. washThe combined organic layers were washed with brine
  12. dry with materialdried over Na2SO4
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customPurification on silica gel (eluting with EtOAc/hexanes, 3:7)

出典と根拠

ORDレコード
ord-663ba5a2f9724428967606fe9ea0a9d9
出典データセット
uspto-grants-2011_06
特許番号
US07960409B2

反応ノート

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