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Water → 5-Benzyl-6-(piperidin-4-yloxy)-isoquinoline

HRID 1022868
ノート
印刷プレビュー

反応式

HRID 1022868 の反応式
O.C(OC([N:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[C:17](Br)=[C:18]3[C:23](=[CH:24][CH:25]=2)[CH:22]=[N:21][CH:20]=[CH:19]3)[CH2:11][CH2:10]1)=O)(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:33]([B-](F)(F)F)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[K+]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:33]([C:17]1[C:16]([O:15][CH:12]2[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]2)=[CH:25][CH:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][N:21]=[CH:22]2)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 23692459Potassium benzyltrifluoroboranuideHCID 576469744-(5-Bromo-isoquinolin-6-yloxy)-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 576469395-Benzyl-6-(piperidin-4-yloxy)-isoquinoline収率 5.5%

試薬・触媒・溶媒 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
HCID 8028Tetrahydrofuran溶媒

実験手順

0.3 mL of water were added to a solution of 81 mg (0.2 mmol) of 4-(5-bromo-isoquinoline-6-yloxy)-piperidin-1-carboxylic acid tert-butyl ester (11), 195 mg (0.6 mmol) of Cs2CO3, 14.6 mg (0.02 mmol) of Pd(dppf)Cl2 and 51 mg (0.26 mmol) of potassium benzyltrifluoroborate in 3 mL of THF. Argon was bubbled through the mixture for 10 minutes and then the reaction was heated to reflux for 16 h (incomplete conversion). After cooling to room temperature water and ethyl acetate were added. The organic layer was separated, dried over Na2SO4. After removal of the solvents 2 mL 5-6 N HCl in isopropanol was added. After 2 h the solvents were distilled off and the remainder was subjected twice to preparative HPLC to give 3.5 mg compound 29 as trifluoroacetate.

後処理

  1. customArgon was bubbled through the mixture for 10 minutes
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 16 h (incomplete conversion)
  4. additionwere added
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. customAfter removal of the solvents 2 mL 5-6 N HCl in isopropanol
  8. additionwas added
  9. distillationAfter 2 h the solvents were distilled off

出典と根拠

ORDレコード
ord-27994516d3ac41088d1c5f6cc59732a3
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08722671B2

反応ノート

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