Sodium Carbonate → HCID 54597166, 화합물

HRID 2174662노트

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HRID 2174662 반응식
[CH2:1]([O:8][C:9]1[C:10]([NH2:16])=[N:11][CH:12]=[C:13](Br)[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[CH:23]([N:26]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=[CH:28][C:27]1=[O:41])([CH3:25])[CH3:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CCC=1>C(#N)C.Cl[Pd]Cl.[Fe].ClCCl>[NH2:16][C:10]1[N:11]=[CH:12][C:13]([C:30]2[CH:29]=[CH:28][C:27](=[O:41])[N:26]([CH:23]([CH3:25])[CH3:24])[CH:31]=2)=[N:14][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

9

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HCID 10340Sodium CarbonateHCID 3524393Cyclopenta-1,4-dien-1-yl(diphenyl)phosphaneHCID 107551623-(Benzyloxy)-5-bromopyrazin-2-amineHCID 580703861-Isopropyl-6-oxo-1,6-dihydropyridine-3-boronic Acid Pinacol Ester

생성물 1

HCID 54597166HCID 54597166, 화합물수율 13.3%

시약·촉매·용매 4

HCID 23925Iron촉매HCID 24290Palladium Chloride촉매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

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온도
100 °C

실험 절차

3-(benzyloxy)-5-bromopyrazin-2-amine (100 mg, 0.358 mmol) was dissolved in acetonitrile (4 mL). Aqueous Na2CO3 solution (462.3 μL of 2 M, 0.9247 mmol), 1-isopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one (146.0 mg, 0.5548 mmol) and cyclopenta-1,4-dien-1-yl(diphenyl)phosphane; dichloromethane; dichloropalladium; iron (75.33 mg, 0.09247 mmol) was added and the reaction mixture was heated for 30 minutes at 100° C. under microwave conditions. The reaction mixture was concentrated in vacuo and the residue was partitioned between DCM and water. The layers were separated and the aqueous further extracted with DCM. The combined organic extract was dried (MgSO4), filtered and concentrated in vacuo. This material was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, and freeze-dried to give the title compound (16 mg, 6.13% Yield). H1 NMR (400.0 MHz, DMSO) δ 1.35 (d, J=6.8 Hz, 6H), 5.10 (m, J=6.8 Hz, 1H), 5.53 (s, 2H), 6.46 (d, J=9.5 Hz, 1H), 7.32 (m, J=7.3 Hz, 1H), 7.38-7.41 (m, 2H), 7.54 (d, J=7.2 Hz, 2H), 7.95 (dd, J=2.5, 9.5 Hz, 1H), 7.98 (s, 1H) and 8.06 (d, J=2.5 Hz, 1H). MS (ES+) 337.0

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between DCM and water
  3. customThe layers were separated
  4. extractionthe aqueous further extracted with DCM
  5. extractionThe combined organic extract
  6. dry with materialwas dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThis material was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]
  10. customThe fractions were collected
  11. customfreeze-dried

출처 및 근거

ORD 기록
ord-b03129a4b43e4e9d97392930e316c033
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062008B2

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