Potassium Carbonate → HCID 59740842, compound

HRID 547368Notes

Reaction equation

HRID 547368 reaction equation
Cl[C:2]1[CH:22]=[CH:21][C:5]([C:6]([NH:8][CH2:9][C:10]2[C:11]([CH2:16][NH:17][C:18](=[O:20])[O-:19])=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:7])=[C:4]([NH:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+].[C:39]1(B(O)O)[CH2:43][CH2:42][CH2:41][CH:40]=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.CN1C(=O)CCC1>[C:39]1([C:2]2[CH:22]=[CH:21][C:5]([C:6]([NH:8][CH2:9][C:10]3[C:11]([CH2:16][NH:17][C:18](=[O:20])[O:19][C:5]([CH3:21])([CH3:6])[CH3:4])=[N:12][CH:13]=[CH:14][CH:15]=3)=[O:7])=[C:4]([NH:23][CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=3)[N:3]=2)[CH2:43][CH2:42][CH2:41][CH:40]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 3861343(Cyclopent-1-en-1-yl)boronic acidHCID 86620629HCID 86620629, compound

Product 1

HCID 59740842HCID 59740842, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of (3-((6-chloro-2-(3-fluorophenethylamino)nicotinamido)methyl)pyridin-2-yl)methylcarbamate (0.10 g, 0.19 mmol), tetrakis(triphenylphosphine)palladium(0) (0.045 g, 0.039 mmol), K2CO3 (0.081 g, 0.59 mmol), cyclopenten-1-yl boronic acid (0.026 g, 0.23 mmol) and NMP (0.2 mL) was sealed in a tube and microwaved at 150° C. for 30 min. The reaction mixture was filtered through a silica plug with EtOAc, washed with H2O, brine, dried (Na2SO4) and concentrated to give tert-butyl (3-((6-cyclopentenyl-2-(3-fluorophenethylamino)nicotinamido)methyl)pyridin-2-yl)methylcarbamate. LC/MS (M+H+) m/z 546.2.

Workup

  1. customwas sealed in a tube
  2. custommicrowaved at 150° C. for 30 min
  3. filtrationThe reaction mixture was filtered through a silica plug with EtOAc
  4. washwashed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e95cb7c2680642f6be3780019d75efaf
Source dataset
uspto-grants-2011_05
Patent number
US07939534B2

Reaction notes

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