Dichloromethane → HCID 67776540, compound

HRID 1037528Notes

Reaction equation

HRID 1037528 reaction equation
Br[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]2[C:4](=[C:5]([C:28]([NH:30][CH3:31])=[O:29])[N:6]([C:14]3[CH:15]=[N:16][C:17]([O:20][C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)=[CH:18][CH:19]=3)[N:7]=2)[CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:40]1([B-](F)(F)F)[CH2:42][CH2:41]1.[K+].C(Cl)Cl>C1(C)C=CC=CC=1.O.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:40]1([C:2]2[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]3[C:4](=[C:5]([C:28]([NH:30][CH3:31])=[O:29])[N:6]([C:14]4[CH:15]=[N:16][C:17]([O:20][C:21]5[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=5)=[CH:18][CH:19]=4)[N:7]=3)[CH:3]=2)[CH2:42][CH2:41]1

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 23697338Potassium cyclopropyltrifluoroborateHCID 67776686HCID 67776686, compound

Product 1

HCID 67776540HCID 67776540, compoundYield 74.5%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A degassed suspension of 5-bromo-2-[6-(4-fluorophenoxy)pyridin-3-yl]-N-methyl-6-nitro-2H-indazole-3-carboxamide (10 mg, 0.021 mmol), potassium phosphate (35 mg, 0.16 mmol), potassium cyclopropyltrifluoroborate (19 mg, 0.13 mmol) and Pd(dppf)Cl2.CH2Cl2 (3 mg, 0.004 mmol) in toluene (1 mL) and water (0.1 mL) was heated under microwave irradiation at 110° C. for 1 h. The reaction mixture was diluted with EtOAc (3 mL), washed with water (1 mL) and brine (1 mL), then dried (MgSO4) and concentrated to dryness. The residue was purified by flash column chromatography eluting with MeOH/DCM (0-10%) to give 5-cyclopropyl-2-[6-(4-fluorophenoxy)pyridin-3-yl]-N-methyl-6-nitro-2H-indazole-3-carboxamide as a tan solid (7 mg, 73%).

Workup

  1. washwashed with water (1 mL) and brine (1 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by flash column chromatography
  5. washeluting with MeOH/DCM (0-10%)

Sources & evidence

ORD record
ord-6270310100214bf0a530b3b9e917620d
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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