Sodium Bicarbonate → HCID 89783055、化合物

HRID 58071

反応式

HRID 58071 の反応式
Br[C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[OH:15][CH2:16][CH2:17][NH:18][C:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:20].[C:30]([O-:33])(O)=[O:31].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:30]([OH:33])([C:11]([F:14])([F:13])[F:12])=[O:31].[OH:15][CH2:16][CH2:17][NH:18][C:19](=[O:20])[C:21]1[CH:26]=[CH:25][C:24]([C:2]2[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]3[C:3]=2[CH:4]=[N:5][NH:6]3)=[CH:23][CH:22]=1

参加物

7

反応物 3

HCID 516892Sodium BicarbonateHCID 247292324-Bromo-6-(trifluoromethyl)-1H-indazoleHCID 44119359{4-[(2-Hydroxyethyl)carbamoyl]phenyl}boronic acid

生成物 2

HCID 6422Trifluoroacetic acidHCID 89783055HCID 89783055、化合物収率 30%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
140 °C

実験手順

A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (0.300 g, 1.132 mmol), (4-((2-hydroxyethyl)carbamoyl)phenyl)boronic acid (0.237 g, 1.132 mmol) and PdCl2(dppf) (0.041 g, 0.057 mmol) in dioxane (10 mL) and aqueous saturated NaHCO3 (3 mL). The resulting yellow suspension was heated at 140° C. for 60 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the crude residue was purified by preparative HPLC, eluting with 40% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 4.5 minutes. The product-containing fractions were combined and volatiles removed in vacuo to give a TFA salt of the title compound as white solid (0.12 g, 30%). 1H NMR (400 MHz, CD3OD) δ ppm 3.56 (t, J=5.81 Hz, 2H), 3.75 (t, J=5.81 Hz, 2H), 7.49 (d, J=1.01 Hz, 1H), 7.78-7.89 (m, 2H), 7.93 (s, 1H), 8.00-8.10 (m, 2H), 8.21-8.32 (m, 1H); ESI-MS m/z [M+H]+ calc'd for C17H14F3N3O2, 350.1. found 350.1.

後処理

  1. concentrationThe reaction mixture was subsequently concentrated
  2. customthe crude residue was purified by preparative HPLC
  3. washeluting with 40% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 4.5 minutes
  4. customvolatiles removed in vacuo

出典と根拠

ORDレコード
ord-499578f0ade742d8a598a93cc082bdb9
出典データセット
uspto-grants-2016_09
特許番号
US09434743B2

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