Potassium Carbonate → HCID 86658462、化合物

HRID 335857ノート

反応式

HRID 335857 の反応式
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]

参加物

11

反応物 5

HCID 11430Potassium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 27627793-bromo-4-fluoropyridineHCID 86640736HCID 86640736、化合物

生成物 1

HCID 86658462HCID 86658462、化合物

試薬・触媒・溶媒 5

HCID 178418397HCID 178418397、化合物触媒HCID 178418807HCID 178418807、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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].

後処理

  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]

出典と根拠

ORDレコード
ord-2d7ceb8ab0ef4e0ca032bd1c40acdecd
出典データセット
uspto-grants-2014_11
特許番号
US08883782B2

反応ノート

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