Potassium Carbonate → HCID 178477701、化合物

HRID 1888253ノート

反応式

HRID 1888253 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]#[N:12])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH:13]1[CH2:18][CH2:17][N:16]([S:19]([CH2:22][CH3:23])(=[O:21])=[O:20])[CH2:15][CH2:14]1.[F:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[C:29]([F:31])[CH:30]=1.C(=O)([O-])[O-:36].[K+].[K+]>O1CCOCC1.O>[F:24][C:25]1[CH:26]=[C:27]([C:2]2[CH:3]=[C:4]3[C:8](=[C:9]([C:11]([NH2:12])=[O:36])[CH:10]=2)[NH:7][N:6]=[C:5]3[CH:13]2[CH2:14][CH2:15][N:16]([S:19]([CH2:22][CH3:23])(=[O:20])=[O:21])[CH2:17][CH2:18]2)[CH:28]=[C:29]([F:31])[CH:30]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 178477688HCID 178477688、化合物2 回

生成物 1

HCID 178477701HCID 178477701、化合物収率 33%

試薬・触媒・溶媒 1

HCID 218864351,4-Dioxane--water (1/1)溶媒

実験手順

Following the general procedure of Example 66, a mixture of 5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indazole-7-carbonitrile (Intermediate 10) (61.3 mg, 0.125 mmols), 3,5-difluorophenyl boronic acid (59 mg, 0.375 mmols), potassium carbonate (104 mg, 0.75 mmol), and chloro(di-2-norbonylphosphine)-(2-dimethylaminomethyl-forrocen-1-yl)palladium (15 mg, 0.025 mmol) in dioxane/water (3/1, 4 mL) was reacted. The reaction mixture was concentrated, redissolved in methylene chloride and filtered. The filtrate was concentrated and the residue was purified by using a Gilson semi-preparative HPLC system, eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) pumped at 25 mL/min to give the title compound (15 mg, 33%)

後処理

  1. customwas reacted
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionredissolved in methylene chloride
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified
  7. washeluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid)

出典と根拠

ORDレコード
ord-935af53868d34e5cafc43464656e5068
出典データセット
uspto-grants-2013_08
特許番号
US08501780B2

反応ノート

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