Potassium Carbonate → HCID 57566680, compound

HRID 1727111Notes

Reaction equation

HRID 1727111 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[CH:15]=2)[C:10](I)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(O)C.O.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>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[CH:15]=2)[C:10]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[Cl:26])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 57566681HCID 57566681, compound

Product 1

HCID 57566680HCID 57566680, compoundYield 68.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (Ph3P)4Pd (36 mg, 0.03 mmol) in dioxane ( 4 mL) under Argon was added 6-(2-Fluoro-phenoxy)-3-iodo-indazole-1-carboxylic acid tert-butyl ester (140 mg, 0.3 mmol) and the solution was stirred for 10 min, then 2-chlorophenyl boronic acid (96.4 mg, 0.6 mmol) in ethanol (1.2 mL) was added. After 10 min potassium carbonate (132 mg, 0.9 mmol) in water (0.4 mL) was added and the mixture was stirred at 85° C. under Argon for 18 h. The mixture was cooled to room temperature, filtered through Celite, partitioned between water and EtOAc, the separated organic phase was dried over Na2SO4 filtered, concentrated and the residue was purified by flash chromatography eluting with Hex:EtOAc 9:1 to yield 90 mg of 3-(2-Chloro-phenyl)-6-(2-fluoro-phenoxy)-indazole-1-carboxylic acid tert-butyl ester: MS: 345 (M+H).

Workup

  1. stirringthe mixture was stirred at 85° C. under Argon for 18 h
  2. filtrationfiltered through Celite
  3. custompartitioned between water and EtOAc
  4. dry with materialthe separated organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified by flash chromatography
  8. washeluting with Hex

Sources & evidence

ORD record
ord-c7f5e8d829154846a9f3116e83fc5ccf
Source dataset
uspto-grants-2009_02
Patent number
US07495015B2

Reaction notes

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