Potassium Carbonate → HCID 66691549, compound

HRID 472842Notes

Reaction equation

HRID 472842 reaction equation
[Br:1][C:2]1[C:3]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:4][N:5]2[C:10](Cl)=[C:9]([CH:12]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:13]([O:15][CH3:16])=[O:14])[C:8]([CH3:22])=[N:7][C:6]=12.[F:29][C:30]1[CH:31]=[C:32](B2OC(C)(C)C(C)(C)O2)[C:33]([CH3:40])=[C:34]2[C:39]=1[O:38][CH2:37][CH2:36][CH2:35]2.C([O-])([O-])=O.[K+].[K+]>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.CN(C=O)C>[Br:1][C:2]1[C:3]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:4][N:5]2[C:10]([C:32]3[C:33]([CH3:40])=[C:34]4[C:39](=[C:30]([F:29])[CH:31]=3)[O:38][CH2:37][CH2:36][CH2:35]4)=[C:9]([CH:12]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:13]([O:15][CH3:16])=[O:14])[C:8]([CH3:22])=[N:7][C:6]=12

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 596067662-(8-Fluoro-5-methylchroman-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86670280HCID 86670280, compound

Product 1

HCID 66691549HCID 66691549, compoundYield 9.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a 2-5 ml microwave tube was added methyl 2-(3-bromo-7-chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (290 mg, 0.621 mmol), tetrakis(triphenylphosphine)palladium(0) (71.8 mg, 0.062 mmol), 2-(8-fluoro-5-methylchroman-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (200 mg, 0.683 mmol), DMF (2 mL) followed by 2M K2CO3 solution (200 μl). The reaction mixture was heated in a microwave reactor at 110° C. for 40 min. The reaction mixture was filtered and the filtrate was purified by silica gel chromatography to afford (35 mg, 9.4%) of the title compound. 1H NMR (500 MHz, CHLOROFORM-d) δ 7.90 (dd, J=8.1, 1.4 Hz, 2H), 7.53-7.32 (m, 3H), 6.86 (d, J=10.7 Hz, 1H), 5.02 (s, 1H), 4.48-4.18 (m, 2H), 3.64 (s, 3H), 2.82 (s, 3H), 2.75 (t, J=6.4 Hz, 2H), 2.20-2.12 (m, 2H), 1.84 (s, 3H), 1.16 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f153214a0da44fce8ea2e4341074f009
Source dataset
uspto-grants-2014_01
Patent number
US08633200B2

Reaction notes

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