Sodium Carbonate → HCID 59472154, 화합물

HRID 78564

반응식

HRID 78564 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

HCID 59472154HCID 59472154, 화합물수율 83.4%

시약·촉매·용매 3

HCID 24290Palladium Chloride촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-90c9a609f1164fa2800eafbbc9caf6e9
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841308B2

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