Potassium Phosphate, Tribasic → HCID 70945532、化合物

HRID 517973ノート

反応式

HRID 517973 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([C:31]([F:34])([F:33])[F:32])[C:12]([O:15][CH2:16][CH2:17][CH:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)=[N:13][CH:14]=2)O1.[NH2:36][C:37]1[C:38]([C:46]#[N:47])=[N:39][C:40](Cl)=[CH:41][C:42]=1[NH:43][CH3:44].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH2:36][C:37]1[C:42]([NH:43][CH3:44])=[CH:41][C:40]([C:9]2[CH:14]=[N:13][C:12]([O:15][CH2:16][CH2:17][CH:18]3[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])[CH2:22][CH2:23]3)=[C:11]([C:31]([F:32])([F:33])[F:34])[CH:10]=2)=[N:39][C:38]=1[C:46]#[N:47]

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 576575713-Amino-6-chloro-4-methylamino-pyridine-2-carbonitrileHCID 69931721Tert-butyl 4-(2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-yloxy)ethyl)piperidine-1-carboxylate

生成物 1

HCID 70945532HCID 70945532、化合物収率 98.5%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A suspension of tert-butyl 4-(2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-yloxy)ethyl)piperidine-1-carboxylate (8.95 g), 3-amino-6-chloro-4-(methylamino)picolinonitrile (2.29 g), tris(dibenzylideneacetone)dipalladium (0) (0.59 g), tricyclohexylphosphine (0.43 g) and potassium phosphate (5.48 g) in 1,4-dioxane (80 ml) and water (40 ml) was stirred at 100° C. under nitrogen for 2 h. The reaction mixture was cooled and partitioned between water and ethyl acetate, washed with water, brine, dried over sodium sulphate, filtered and concentrated. Purified by Biotage SNAP cartridge KP-Sil column (340 g, heptane:ethyl acetate=1:0, 2:1, 1:1 to 1:2) to give 6.43 g light brown solid as tert-butyl 4-(2-(5-amino-6-cyano-4-(methylamino)-5′-(trifluoromethyl)-2,3′-bipyridin-6′-yloxy)ethyl)piperidine-1-carboxylate (99%, 90% purity).

後処理

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between water and ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurified by Biotage SNAP cartridge KP-Sil column (340 g, heptane:ethyl acetate=1:0, 2:1, 1:1 to 1:2)

出典と根拠

ORDレコード
ord-e86ca147c4974935a51411e0014d74dc
出典データセット
uspto-grants-2015_08
特許番号
US09115126B2

反応ノート

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