1-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 59362938, compound

HRID 1668820Notes

Reaction equation

HRID 1668820 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[C:21]4[CH2:22][CH2:23][CH2:24][C:20]=4[N:19]=[C:18](Cl)[N:17]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4].[CH3:26][N:27]1[C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][CH:29]=[N:28]1>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]>[CH3:1][O:2][C:3]([C:5]1([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[C:21]4[CH2:22][CH2:23][CH2:24][C:20]=4[N:19]=[C:18]([C:30]4[CH:29]=[N:28][N:27]([CH3:26])[CH:31]=4)[N:17]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 49129081-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 59362943HCID 59362943, compound

Product 1

HCID 59362938HCID 59362938, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
100 °C

Procedure

A glass tube was charged with 1-[4-(2-chloro-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid methyl ester (0.5 g, 1.4 mmol), 1-methyl-1H-pyrazole-5-boronic acid pinacol ester (0.42 g, 2 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) (0.081 g, 0.1 mmol) and alternatively purged and backfilled with nitrogen. After addition of anhydrous toluene (10 mL), EtOH (5 mL), and sodium carbonate (2M, 2 mL) the glass tube was sealed and heated at 100° C. under stirring until the reaction was complete as evidenced by the disappearance of starting chloro compound (TLC). The resulting mixture was cooled to a temperature in the range of 15° C. to 40° C., diluted with ethyl acetate (20 mL), filtered through Celite, washed with ethyl acetate, and the combined filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel to afford the title compound as a light yellow solid (0.27 g, 48%).

Workup

  1. customalternatively purged
  2. additionAfter addition of anhydrous toluene (10 mL), EtOH (5 mL), and sodium carbonate (2M, 2 mL) the glass tube
  3. customwas sealed
  4. temperatureThe resulting mixture was cooled to a temperature in the range of 15° C. to 40° C.
  5. additiondiluted with ethyl acetate (20 mL)
  6. filtrationfiltered through Celite
  7. washwashed with ethyl acetate
  8. concentrationthe combined filtrate was concentrated under reduced pressure
  9. customThe residue was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-6d662895fc964d4986127ae93b14a8fb
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

Loading…