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

HRID 1037564노트

반응식

HRID 1037564 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매

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온도
8 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4538c039bd16469d8c7ac3202aa872d6
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546389B2

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