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

HRID 1784821ノート

反応式

HRID 1784821 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178482708HCID 178482708、化合物触媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6703728128714fcc8e5ef29e680462c9
出典データセット
uspto-grants-2009_03
特許番号
US07504401B2

反応ノート

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