Potassium Phosphate, Tribasic → [3-Hydroxy-5-(1H-indol-4-YL)-phenyl]-(6-hydroxymethyl-pyridin-3-YL)-methanone

HRID 1784821노트

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HRID 1784821 반응식
COC1C=CC(C[O:8][C:9]2[CH:10]=[C:11]([CH:25]=[C:26]([C:28]3[CH:36]=[CH:35][CH:34]=[C:33]4[C:29]=3[CH:30]=[CH:31][N:32]4[Si](C(C)C)(C(C)C)C(C)C)[CH:27]=2)[C:12]([C:14]2[CH:15]=[CH:16][C:17]([CH2:20][O:21]C(=O)C)=[N:18][CH:19]=2)=[O:13])=CC=1.BrC1C=C(C=C(OCC2C=CC(OC)=CC=2)C=1)C(C1C=CC(COC(=O)C)=NC=1)=O.CC1(C)C(C)(C)OB(C2C=CC=C3C=2C=CN3[Si](C(C)C)(C(C)C)C(C)C)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C(Cl)Cl.Cl[Pd-](P(C1CC2CC1CC2)C1CC2CC1CC2)C1C=CC=CC=1C1C=CC=CC=1N(C)C>[OH:8][C:9]1[CH:10]=[C:11]([C:12]([C:14]2[CH:19]=[N:18][C:17]([CH2:20][OH:21])=[CH:16][CH:15]=2)=[O:13])[CH:25]=[C:26]([C:28]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:29]=2[CH:30]=[CH:31][NH:32]3)[CH:27]=1

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 27955744-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1-(triisopropylsilyl)-1H-indoleHCID 68844868Acetic acid 5-[3-(4-methoxy-benzyloxy)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-benzoyl]-pyridin-2-ylmethyl esterHCID 68844896Acetic acid 5-[3-bromo-5-(4-methoxy-benzyloxy)-benzoyl]-pyridin-2-ylmethyl ester

생성물 1

HCID 15604424[3-Hydroxy-5-(1H-indol-4-YL)-phenyl]-(6-hydroxymethyl-pyridin-3-YL)-methanone

시약·촉매·용매 3

HCID 178482708HCID 178482708, 화합물촉매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매2회

실험 절차

Acetic acid 5-[3-(4-methoxy-benzyloxy)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-benzoyl]-pyridin-2-ylmethyl ester. To the mixture of acetic acid 5-[3-bromo-5-(4-methoxy-benzyloxy)-benzoyl]-pyridin-2-ylmethyl ester (145 mg, 0.308 mmol) and chloro(di-2-norbornylphosphino)(2′dimethylamino-1,1′-biphenyl-2-yl)palladium (II) (15 mg) in dioxane (6 mL) under nitrogen was added a solution of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-indole (129 mg, 0.324 mmol) in dioxane (6 mL), followed by 2M K3PO4 (0.3 mL, 0.6 mmol). The resulting solution was heated at reflux for 24 hr. The reaction mixture was then diluted with methylene chloride and the organic phase washed with brine, dried, and concentrated. After removal of the solvents, the crude product was purified by flash chromatography (3:1 hexane/EtOAc) to afford the titled product which was carried to the next step without further purification.

후처리

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 24 hr
  3. washthe organic phase washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customAfter removal of the solvents
  7. customthe crude product was purified by flash chromatography (3:1 hexane/EtOAc)

출처 및 근거

ORD 기록
ord-6703728128714fcc8e5ef29e680462c9
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504401B2

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