Methanol → HCID 68162139, compound

HRID 2400351Notes

Reaction equation

HRID 2400351 reaction equation
C(OC(=O)[NH:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12](I)=[CH:13][N:14]=[C:8]2[CH:7]=1)C.ClC1C=CN2C([C:27]3[CH:28]=[C:29]([NH:33][C:34]([NH:36][CH2:37][C:38]([F:41])([F:40])[F:39])=[O:35])[CH:30]=[CH:31][CH:32]=3)=CN=C2C=1.C([O-])([O-])=O.[K+].[K+].CO>C1(C)C=CC=CC=1.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.O.CCO>[NH2:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:31]3[CH:30]=[C:29]([NH:33][C:34]([NH:36][CH2:37][C:38]([F:39])([F:40])[F:41])=[O:35])[CH:28]=[CH:27][CH:32]=3)=[CH:13][N:14]=[C:8]2[CH:7]=1

Participants

9

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 574976981-(3-(7-Chloroimidazo[1,2-a]pyridin-3-yl)phenyl)-3-(2,2,2-trifluoroethyl)ureaHCID 67029422HCID 67029422, compound

Product 1

HCID 68162139HCID 68162139, compoundYield 11.5%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of (3-Iodo-imidazo[1,2-a]pyridin-7-yl)carbamic acid ethyl ester (100 mg, 0.30 mmol) in toluene (0.5 ml) was added 1-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-urea (described in procedure A4) (126 mg, 0.36 mmol), K2CO3 (250 mg, 1.80 mmol), MeOH (0.5 ml), EtOH (0.5 ml) and water (0.7 ml) [reaction degassed by bubbling N2 through]. Bis(tri-tert-butylphosphine)palladium (0) (1.5 mg, 0.003 mmol) was added and the reaction was heated in a CEM discover microwave synthesizer (300W) at 135° C. for 30 min. The mixture was partitioned between water and EtOAc and the organic fraction was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by preparative HPLC to give the product (12 mg). MS: [M+H]+=350.

Workup

  1. temperaturethe reaction was heated in a CEM
  2. customat 135° C.
  3. customfor 30 min
  4. customThe mixture was partitioned between water and EtOAc
  5. dry with materialthe organic fraction was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-6a30c3b6e9e7430096ca373e1cadf066
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

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