Potassium Carbonate → HCID 57551786, compound

HRID 907291Notes

Reaction equation

HRID 907291 reaction equation
[CH:1]1([NH:4][C:5](=[O:23])[C:6]2[CH:11]=[C:10](B3OC(C)(C)C(C)(C)O3)[C:9]([CH3:21])=[C:8]([F:22])[CH:7]=2)[CH2:3][CH2:2]1.[CH2:24]([N:31]1[CH:40]=[C:39]([C:41]([NH:43][CH2:44][CH2:45][N:46]([CH3:48])[CH3:47])=[O:42])[C:38]2[C:33](=[CH:34][CH:35]=[C:36](Br)[CH:37]=2)[C:32]1=[O:50])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(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>[CH2:24]([N:31]1[CH:40]=[C:39]([C:41]([NH:43][CH2:44][CH2:45][N:46]([CH3:47])[CH3:48])=[O:42])[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([C:10]3[CH:11]=[C:6]([C:5](=[O:23])[NH:4][CH:1]4[CH2:2][CH2:3]4)[CH:7]=[C:8]([F:22])[C:9]=3[CH3:21])[CH:37]=2)[C:32]1=[O:50])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 21914563N-cyclopropyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 57551824HCID 57551824, compound

Product 1

HCID 57551786HCID 57551786, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a degassed mixture of N-cyclopropyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.1 g) [prepared as described in WO 06110173], the product of step ii) (0.09 g) and potassium carbonate (0.06 g) in DMF (5 mL) under nitrogen, was added tetrakis(triphenylphosphine)palladium(0) (0.02 g) and the mixture stirred at 80° C. for 16 hours. The reaction mixture was concentrated to dryness and the crude product was purified (SiO2, elution with 90:10:0.1 dichloromethane: methanol: triethylamine) and by HPLC. The fractions containing product were concentrated to dryness and the residue crystallised from acetonitrile to afford the title compound as a solid (0.04 g).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe crude product was purified
  3. wash(SiO2, elution with 90:10:0.1 dichloromethane: methanol: triethylamine)
  4. additionThe fractions containing product
  5. concentrationwere concentrated to dryness
  6. customthe residue crystallised from acetonitrile

Sources & evidence

ORD record
ord-0022f0c289dd4fb787d511aba07cd74c
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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