Benzyl Alcohol → HCID 131735484、化合物

HRID 634431ノート

反応式

HRID 634431 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[C:5]([I:8])=[N:6][CH:7]=1.[CH2:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.CCCCCCC>[CH3:11][CH2:10][O:17][C:4]([CH3:5])=[O:9].[CH2:10]([O:9][C:4]1[C:5]([I:8])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

7

反応物 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 226029855-Bromo-2-iodopyridin-3-ol

生成物 1

HCID 131735484HCID 131735484、化合物収率 92%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8900Heptane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 5-bromo-2-iodopyridin-3-ol (0.700 g, 2.334 mmol, prepared according to Bioorg. Med. Chem. Lett. 2013, 2, 6784, which is incorporated herein by reference in its entirety) in dry THF (10 ml), previously cooled to 0° C., benzyl alcohol (0.728 ml, 7.00 mmol), triphenylphosphine (PPh3) (2.095 ml, 7.00 mmol) and diisopropyl azodicarboxylate (1.287 ml, 6.54 mmol) were added. The reaction was stirred for 4 h at room temperature. Solvent was removed and the product was purified by Biotage Si 50 g with a gradient of heptane and EtOAc 3-(benzyloxy)-5-bromo-2-iodopyridine (Intermediate G25.1, 835 mg, 2.141 mmol, 92% yield) as a white foam.

後処理

  1. customSolvent was removed

出典と根拠

ORDレコード
ord-b9eb90f9b7a346bf99552587be3751df
出典データセット
uspto-grants-2016_04
特許番号
US09321776B2

反応ノート

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