Cesium carbonate → 6-(3-aminophenyl)-2-(4-fluorophenyl)-N-methyl-2H-indazole-3-carboxamide

HRID 1037564ノート

反応式

HRID 1037564 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[C:6]=2[C:18]([NH:20][CH3:21])=[O:19].B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:7][C:11]1[CH:12]=[C:13]([C:2]2[CH:3]=[CH:4][C:5]3[C:9]([CH:10]=2)=[N:8][N:7]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[C:6]=3[C:18]([NH:20][CH3:21])=[O:19])[CH:14]=[CH:15][CH:16]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 61668Boronic AcidHCID 677756736-bromo-2-(4-fluorophenyl)-N-methyl-2H-indazole-3-carboxamide

生成物 1

HCID 569629266-(3-aminophenyl)-2-(4-fluorophenyl)-N-methyl-2H-indazole-3-carboxamide収率 222%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒

反応条件

温度
8 °C

実験手順

A suspension of compound (xvii) (10 mg, 0.03 mmol), boronic acid (5.9 mg, 0.04 mmol), cesium carbonate (14 mg, 0.04 mmol) and tetrakis(triphenylphosphine)palladium (2 mg, 0.001 mmol) in ethanol (2 mL) were degassed and stirred under an atmosphere of nitrogen then heated to 8° C. After 3 h the reaction mixture was concentrated and the residue was partitioned between EtOAc (25 mL) and water (15 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (3×15 mL). The combined organics were washed with brine (15 mL), dried (MgSO4) and concentrated to give 6-(3-aminophenyl)-2-(4-fluorophenyl)-N-methyl-2H-indazole-3-carboxamide (16) (12 mg) as a pale brown oil. The crude material was used directly. ESI-MS m/z calculated for [M+H]+: 361.13; found: 361.14.

後処理

  1. customwere degassed
  2. concentrationAfter 3 h the reaction mixture was concentrated
  3. customthe residue was partitioned between EtOAc (25 mL) and water (15 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with EtOAc (3×15 mL)
  6. washThe combined organics were washed with brine (15 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-4538c039bd16469d8c7ac3202aa872d6
出典データセット
uspto-grants-2013_10
特許番号
US08546389B2

反応ノート

読み込み中…