Potassium Phosphate, Tribasic → HCID 71239958, 화합물

HRID 1753765노트

반응식

HRID 1753765 반응식
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

참가 물질

8

반응물 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, 화합물

생성물 1

HCID 71239958HCID 71239958, 화합물

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매2회HCID 3776Isopropanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-24cdc4025f72497e8ae30c338f5abba6
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09168245B2

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