Sodium Carbonate → HCID 58102398, 화합물

HRID 470571노트

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HRID 470571 반응식
C([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[CH:13]=[CH:12][N:11]([CH:14]2[CH2:16][CH2:15]2)[C:10](=[O:17])[CH:9]=1.[OH:18][C:19]([CH3:53])([CH3:52])[CH2:20][C@@:21]1([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[O:26][C:25](=[O:27])[N:24]([C@H:28]([C:30]2[CH:35]=[CH:34][C:33](B3OC(C)(C)C(C)(C)O3)=[CH:32][C:31]=2[CH3:45])[CH3:29])[CH2:23][CH2:22]1>CN(C)C=O>[CH:14]1([N:11]2[CH:12]=[CH:13][C:8]([C:33]3[CH:34]=[CH:35][C:30]([C@@H:28]([N:24]4[CH2:23][CH2:22][C@:21]([CH2:20][C:19]([OH:18])([CH3:53])[CH3:52])([C:46]5[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=5)[O:26][C:25]4=[O:27])[CH3:29])=[C:31]([CH3:45])[CH:32]=3)=[CH:9][C:10]2=[O:17])[CH2:16][CH2:15]1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 58102383HCID 58102383, 화합물HCID 596356474-Bromo-1-cyclopropylpyridin-2(1H)-one

생성물 1

HCID 58102398HCID 58102398, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

2 M aqueous Na2CO3 solution (0.41 mL) was added to a mixture of 4-bromo-1-cyclopropyl-1H-pyridin-2-one (0.11 g) and (S)-6-(2-hydroxy-2-methyl-propyl)-3-{(S)-1-[2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-6-phenyl-[1,3]oxazinan-2-one (0.20 g) in N,N-dimethylformamide (2 mL). The resulting mixture was sparged with argon for 10 min prior to the addition of [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium(II) dichloromethane complex (33 mg). The mixture was heated to 100° C. and stirred at this temperature overnight. After cooling the mixture to ambient temperature, water was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with water and brine and dried (MgSO4). The solvent was evaporated and the residue was purified by HPLC on reversed phase (methanol/water/NH4OH) to afford the title compound. Yield: 0.13 g (64% of theory); LC-MS (Method 5): tR=3.43 min; Mass spectrum (ESI+): m/z=501 [M+H]+.

후처리

  1. customThe resulting mixture was sparged with argon for 10 min
  2. additionto the addition of [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium(II) dichloromethane complex (33 mg)
  3. temperatureAfter cooling the mixture to ambient temperature
  4. additionwater was added
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washThe combined organic extracts were washed with water and brine
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated
  9. customthe residue was purified by HPLC on reversed phase (methanol/water/NH4OH)

출처 및 근거

ORD 기록
ord-9b186f11d7d14eb287105a09bc80f174
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629138B2

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