Potassium Phosphate, Tribasic → HCID 70945532, 화합물

HRID 517973노트

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HRID 517973 반응식
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]

참가 물질

8

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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

생성물 1

HCID 70945532HCID 70945532, 화합물수율 98.5%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e86ca147c4974935a51411e0014d74dc
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115126B2

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