Potassium Carbonate → HCID 86658462, 화합물

HRID 335857노트

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HRID 335857 반응식
C([O-])(=O)C.[K+].FC(F)(F)S(O[C:12]1[CH:13]=[C:14]2[C@@:25]3([CH2:29][O:28][C:27]([NH2:30])=[N:26]3)[C:24]3[C:19](=[N:20][CH:21]=[C:22](C#CC4(C)COC4)[CH:23]=3)[O:18][C:15]2=[CH:16][CH:17]=1)(=O)=O.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.BrC1C=NC=CC=1F.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[O:28]1[CH2:29][C:25]2([C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[O:18][C:15]3[C:14]2=[CH:13][CH:12]=[CH:17][CH:16]=3)[N:26]=[C:27]1[NH2:30]

참가 물질

11

반응물 5

HCID 11430Potassium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 27627793-bromo-4-fluoropyridineHCID 86640736HCID 86640736, 화합물

생성물 1

HCID 86658462HCID 86658462, 화합물

시약·촉매·용매 5

HCID 178418397HCID 178418397, 화합물촉매HCID 178418807HCID 178418807, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

A solution of potassium acetate (0.210 g, 2.140 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.022 g, 0.027 mmol), (S)-2′-amino-3-((3-methyloxetan-3-yl)ethynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-7-yl trifluoromethanesulfonate (0.265 g, 0.535 mmol), and bis(pinacolato)diboron (0.143 g, 0.562 mmol) in 5 mL DMF was heated to 100° C. for 3 hours. Pd(PPh3)4 (0.031 g, 0.027 mmol) was added, followed by 3-bromo-4-fluoropyridine (0.141 g, 0.802 mmol), potassium carbonate (0.296 g, 2.140 mmol), and 2 mL water. The reaction mixture was capped with argon and was heated to 100° C. for 2 hours. After cooling to RT, the reaction mixture was diluted with EtOAc and was washed sequentially with water and brine. The organics were dried over MgSO4 and concentrated. Purification of the crude residue by column chromatography [0-100% (9:1 CH2Cl2:MeOH)/CH2Cl2] then HPLC (10-90% MeCN/H2O) provided (S)-7-(4-fluoropyridin-3-yl)-3-(3-methyloxetan-3-yl)ethynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine. MS m/z=443.0 [M+H].

후처리

  1. customThe reaction mixture was capped with argon
  2. temperatureAfter cooling to RT
  3. washwas washed sequentially with water and brine
  4. dry with materialThe organics were dried over MgSO4
  5. concentrationconcentrated
  6. customPurification of the crude residue by column chromatography [0-100% (9:1 CH2Cl2:MeOH)/CH2Cl2]

출처 및 근거

ORD 기록
ord-2d7ceb8ab0ef4e0ca032bd1c40acdecd
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883782B2

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