Potassium Phosphate, Tribasic → HCID 70945481、化合物

HRID 517998ノート

反応式

HRID 517998 の反応式
[CH3:1][N:2]([CH2:10][CH2:11][O:12][C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][C:16](B2OC(C)(C)C(C)(C)O2)=[CH:15][N:14]=1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[NH2:32][C:33]1[C:34]([C:42]#[N:43])=[N:35][C:36](Cl)=[CH:37][C:38]=1[NH:39][CH3:40].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]>[NH2:32][C:33]1[C:38]([NH:39][CH3:40])=[CH:37][C:36]([C:16]2[CH:15]=[N:14][C:13]([O:12][CH2:11][CH2:10][N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:6])([CH3:7])[CH3:8])=[C:18]([C:19]([F:20])([F:21])[F:22])[CH:17]=2)=[N:35][C:34]=1[C:42]#[N:43]

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 576575713-Amino-6-chloro-4-methylamino-pyridine-2-carbonitrileHCID 69932325HCID 69932325、化合物

生成物 1

HCID 70945481HCID 70945481、化合物収率 49%

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 methyl(2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-yloxy)ethyl)carbamate (440 mg), 3-amino-6-chloro-4-(methylamino)picolinonitrile (135 mg), tris(dibenzylideneacetone)dipalladium (0) (34.9 mg), tricyclohexylphosphine (25.7 mg) and potassium phosphate (327 mg) in 1,4-dioxane (10 ml) and water (5 ml) was stirred at 100° C. for 2 h. The reaction mixture was cooled and partitioned between water and ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered and concentrated. Purified by Biotage SNAP cartridge KP-Sil column (25 g, heptane:ethyl acetate=1:0, 3:1, 2:1, 1:1 to 1:2) to give 170 mg orange amorphous as tert-butyl 2-(5-amino-6-cyano-4-(methylamino)-5′-(trifluoromethyl)-2,3′-bipyridin-6′-yloxy)ethyl(methyl)carbamate (49%).

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 sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurified by Biotage SNAP cartridge KP-Sil column (25 g, heptane:ethyl acetate=1:0, 3:1, 2:1, 1:1 to 1:2)

出典と根拠

ORDレコード
ord-17b238368e8745368278ae3dc4d6fdcb
出典データセット
uspto-grants-2015_08
特許番号
US09115126B2

反応ノート

読み込み中…