Ethyl Acetate → HCID 86713608、化合物

HRID 2404074ノート

反応式

HRID 2404074 の反応式
I[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]#[N:12])[C:5]2=[N:4][CH:3]=1.[CH:13]([O:16][C:17]1[CH:18]=[C:19]([NH:32][C:33]([NH:35][CH2:36][C:37]([F:40])([F:39])[F:38])=[O:34])[CH:20]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:22]=1)([CH3:15])[CH3:14].C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>O1CCOCC1.[Cl-].[Na+].O.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(Cl)Cl>[C:11]([C:10]1[C:5]2[N:6]([C:2]([C:21]3[CH:20]=[C:19]([NH:32][C:33]([NH:35][CH2:36][C:37]([F:38])([F:39])[F:40])=[O:34])[CH:18]=[C:17]([O:16][CH:13]([CH3:15])[CH3:14])[CH:22]=3)=[CH:3][N:4]=2)[CH:7]=[CH:8][CH:9]=1)#[N:12]

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 58081529HCID 58081529、化合物HCID 717572643-Iodo-imidazo[1,2-a]pyridine-8-carbonitrile

生成物 1

HCID 86713608HCID 86713608、化合物収率 32.1%

試薬・触媒・溶媒 3

HCID 178418807HCID 178418807、化合物触媒HCID 312751,4-Dioxane溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
110 °C

実験手順

To a mixture of 3-iodoimidazo[1,2-a]pyridine-8-carbonitrile (100 mg, 373 μmol), 1-(3-isopropoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-(2,2,2-trifluoroethyl)urea (90 mg, 224 μmol), PdCl2(dppf)-CH2Cl2 Adduct (30.5 mg, 37.3 μmol) in Dioxane (3 ml), was added 2M Na2CO3 (0.559 ml, 1119 μmol). The vial was degassed for 5 minutes then capped and heated to 110° C. for 30 minutes in microwave. After cooling to ambient temperature reaction was partioned between EtOAc and brine, separated and organics washed with brinex2. Combined organics were dried directly on to silica and purified via flash chromatography (0-100% Hex/EtOAc; 12 g column). Recovered the title compound (30 mg, 71.9 μmol, 32.1% yield) as a brown solid. MS (ES+) C20H18F3N5O2 requires: 417. found: 418 [M+H]+.

後処理

  1. customThe vial was degassed for 5 minutes
  2. customthen capped
  3. temperatureAfter cooling to ambient temperature
  4. customreaction
  5. customseparated
  6. washorganics washed with brinex2
  7. customCombined organics were dried directly on to silica
  8. custompurified via flash chromatography (0-100% Hex/EtOAc; 12 g column)

出典と根拠

ORDレコード
ord-c51db83a8f304ac09ee222863fa6a382
出典データセット
uspto-grants-2014_08
特許番号
US08802697B2

反応ノート

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