Potassium Carbonate → HCID 178477698、化合物

HRID 1888252ノート

反応式

HRID 1888252 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]=[CH:29][C:30]=1[F:31].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]=[CH:29][C:30]=1[F:31]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 27343373,4-Difluorobenzeneboronic acidHCID 178477688HCID 178477688、化合物2 回

生成物 1

HCID 178477698HCID 178477698、化合物収率 24%

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) (50 mg, 0.102 mmols), 3,4-difluorophenyl boronic acid (48 mg, 0.306 mmols), potassium carbonate (84 mg, 0.612 mmol), and chloro(di-2-norbonylphosphino)-(2-dimethylaminomethyl-ferrocen-1-yl)paladium (3 mg) 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 (11 mg, 24%)

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-954482f1b59d4f86b19fa73a127b4ec9
出典データセット
uspto-grants-2013_08
特許番号
US08501780B2

反応ノート

読み込み中…