Potassium Carbonate → HCID 66576591, compound

HRID 1405192Notes

Reaction equation

HRID 1405192 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:10]=2)[N:3]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[C:23]([O:30][CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C(OCC)(=O)C.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]>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:10]=3)[N:3]=2)=[C:23]([O:30][CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[CH:22]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 219563434-chloro-N-{3-[(methylsulfonyl)methyl]phenyl}-1,3,5-triazin-2-amineHCID 53216478[4-Chloro-2-(cyclopentyloxy)phenyl]boronic acid

Product 1

HCID 66576591HCID 66576591, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A batch with crude crude 4-chloro-N-{3-[(methylsulfonyl)methyl]phenyl}-1,3,5-triazin-2-amine (175 mg), [4-chloro-2-(cyclopentyloxy)phenyl]boronic acid (141 mg; 0.59 mmol; Combi-Blocks Inc.) and [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride (72 mg; 0.09 mmol) in 1,2-dimethoxyethane (2.0 mL) and 2M solution of potassium carbonate (0.6 mL) was degassed using argon. The batch was stirred under argon for 60 minutes at 100° C. After cooling the batch was diluted with ethyl acetate. The organic phase was filtered using a Whatman filter and concentrated. The residue was purified by preparative HPLC.

Workup

  1. temperatureAfter cooling the batch
  2. filtrationThe organic phase was filtered
  3. filtrationfilter
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-21d4568740ff4bc0a104e5fa4bfc9e77
Source dataset
uspto-grants-2014_12
Patent number
US08916557B2

Reaction notes

Loading…