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

HRID 1037564Notes

Reaction equation

HRID 1037564 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
8 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4538c039bd16469d8c7ac3202aa872d6
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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