Sodium Carbonate → 3-Amino-6-(pyridin-3-yl)pyrazine-2-carboxylic acid

HRID 2204786ノート

反応式

HRID 2204786 の反応式
[NH2:1][C:2]1[C:3]([C:9]([O:11]C)=[O:10])=[N:4][C:5](Br)=[CH:6][N:7]=1.C(B(CC)[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.Cl[Pd]Cl.CCOC(C)=O>[NH2:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:6][N:7]=1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylateHCID 6428513-(Diethylboryl)pyridine

生成物 1

HCID 594721543-Amino-6-(pyridin-3-yl)pyrazine-2-carboxylic acid収率 83.4%

試薬・触媒・溶媒 3

HCID 24290Palladium Chloride触媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of methyl 3-amino-6-bromo-pyrazine-2-carboxylate (8 g, 34.48 mmol), diethyl-(3-pyridyl)borane (6.084 g, 41.38 mmol), dichloropalladium; triphenylphosphane (1.210 g, 1.724 mmol) and disodium carbonate (51.70 mL of 2 M, 103.4 mmol) in DME (100 mL) were heated overnight at 80° C. The reaction mixture was cooled and EtOAc was added. The resultant precipitate was collected, treated with water and the resultant suspension heated and filtered hot. The solution was then allowed to cool and acidified with AcOH to approx pH 5. The precipitate was collected, washed with MeOH and dried to yield the product as a yellow powder (6.22 g, 83% Yield). 1H NMR (400.0 MHz, DMSO) d 7.49 (dd, J=4.8, 7.4 Hz, 1H), 7.60 (s, 2H), 8.44 (d, J=7.6 Hz, 1H), 8.57 (d, J=3.7 Hz, 1H), 8.97 (s, 1H) and 9.27 (s, 1H) ppm; MS (ES+) 217

後処理

  1. temperatureThe reaction mixture was cooled
  2. customThe resultant precipitate was collected
  3. additiontreated with water
  4. temperaturethe resultant suspension heated
  5. filtrationfiltered hot
  6. temperatureto cool
  7. customThe precipitate was collected
  8. washwashed with MeOH
  9. customdried

出典と根拠

ORDレコード
ord-ddbd0500147a44f5bf4ac0a41abb9055
出典データセット
uspto-grants-2016_06
特許番号
US09365557B2

反応ノート

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