Potassium Phosphate, Tribasic → HCID 71239958、化合物

HRID 1753765ノート

反応式

HRID 1753765 の反応式
Br[C:2]1[CH:7]=[C:6]([C:8]2[O:12][CH:11]=[N:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[CH3:13][O:14][C:15]1[C:20](B2OC(C)(C)C(C)(C)O2)=[C:19]([CH3:30])[CH:18]=[CH:17][N:16]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN(C1C(C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=CC=CC=1)C>CC(O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:13][O:14][C:15]1[C:20]([C:2]2[CH:7]=[C:6]([C:8]3[O:12][CH:11]=[N:10][CH:9]=3)[CH:5]=[CH:4][N:3]=2)=[C:19]([CH3:30])[CH:18]=[CH:17][N:16]=1

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 712410112-Methoxy-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 86724050HCID 86724050、化合物

生成物 1

HCID 71239958HCID 71239958、化合物

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒2 回HCID 3776Isopropanol溶媒

実験手順

An oven-dried flask under argon was charged with the 2-bromo-4-oxazol-5-yl-pyridine (Intermediate II-c, 461 mg, 2.07 mmol), 2-methoxy-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine V-d (510 mg, 2.07 mmol), K3PO4 (2.82 g, 13.3 mmol), Pd(OAc)2 (51 mg, 0.225 mmol), Davephos (89 mg, 0.225 mmol) in iPrOH (5 mL) and water (3 mL). After 40 min at 100° C., the mixture was cooled to room temperature, diluted with water and extracted with EtOAc then washed with brine. The organics were dried (MgSO4), filtered and evaporated before purification by column chromatography (SiO2, 30% to 100% EtOAc in cyclohexane) to afford the desired product V-e as an off-white solid (240 mg, 43%). 1H NMR (300 MHz, CDCl3) δ 8.78 (d, J=4.8 Hz, 1H), 8.10 (d, J=4.8 Hz, 1H), 8.01 (s, 1H), 7.59 (d, J=4.9 Hz, 2H), 7.51 (d, J=4.9 Hz, 1H), 6.86 (d, J=4.9 Hz, 1H), 3.88 (s, 3H), 2.16 (s, 3H).

後処理

  1. extractionextracted with EtOAc
  2. washthen washed with brine
  3. dry with materialThe organics were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated before purification by column chromatography (SiO2, 30% to 100% EtOAc in cyclohexane)

出典と根拠

ORDレコード
ord-24cdc4025f72497e8ae30c338f5abba6
出典データセット
uspto-grants-2015_10
特許番号
US09168245B2

反応ノート

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