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3,4-dihydro-2H-pyran → N-[4-[[3-(3,4-Dihydro-2H-pyran-2-yl)-2-pyridinyl]oxy]phenyl]-2-pyridinamine

HRID 473659
ノート
印刷プレビュー

反応式

HRID 473659 の反応式
Cl.Br[C:3]1[C:4]([O:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[CH:12][CH:11]=2)=[N:5][CH:6]=[CH:7][CH:8]=1.C1(N(C)C2CCCCC2)CCCCC1.[O:37]1[CH:42]=[CH:41][CH2:40][CH2:39][CH2:38]1>[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.O1CCOCC1>[O:37]1[CH:38]=[CH:39][CH2:40][CH2:41][CH:42]1[C:3]1[C:4]([O:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[CH:12][CH:11]=2)=[N:5][CH:6]=[CH:7][CH:8]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 80803,4-dihydro-2H-pyranHCID 24210N-Methyl dicyclohexylamineHCID 67425919N-(4-(3-Bromopyridin-2-yloxy)phenyl)pyridin-2-amine hydrochloride

生成物 1

HCID 59374292N-[4-[[3-(3,4-Dihydro-2H-pyran-2-yl)-2-pyridinyl]oxy]phenyl]-2-pyridinamine

試薬・触媒・溶媒 2

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)触媒
HCID 31275
1,4-Dioxane
溶媒

反応条件

温度
105 °C

実験手順

To a 25 mL microwave vial was added Bis(tri-tert-butylphosphine) palladium (0) (101 mg, 0.198 mmol) and N-(4-(3-bromopyridin-2-yloxy)phenyl)pyridin-2-amine hydrochloride (750 mg, 1.981 mmol) before evacuating and backfilling with nitrogen (2×). After addition of Dioxane (5.659 ml), N-cyclohexyl-N-methylcyclohexanamine (0.840 ml, 3.96 mmol), and 3,4-dihydro-2H-pyran (666 mg, 7.92 mmol) was added and the mixture was heated to 105° C. Following complete consumption of the starting material, the reaction mixture was cooled to room temperature and the volatiles were removed under reduced pressure. Following silica gel chromatography, the title compound was obtained as a racemic mixture. MS (ESI, pos. ion) m/z: 346.0. IC50 (uM) 0.064.

後処理

  1. custombefore evacuating
  2. additionwas added
  3. customconsumption of the starting material
  4. temperaturethe reaction mixture was cooled to room temperature
  5. customthe volatiles were removed under reduced pressure

出典と根拠

ORDレコード
ord-c3626ddc923647bab10de00cd13c2f77
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08637500B2

反応ノート

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