1,2-Dimethoxyethane → HCID 86697443, compound

HRID 1844357Notes

Reaction equation

HRID 1844357 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[N:11][N:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]4)=[N:14][C:13]=23)O1.Br[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[N:33]=1.C([O-])([O-])=O.[K+].[K+].COCCOC>CCOC(C)=O.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.O>[CH3:39][O:38][C:34]1[N:33]=[C:32]([C:9]2[CH:10]=[N:11][N:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:19][CH2:20][N:21]([C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25])[CH2:22][CH2:23]4)=[N:14][C:13]=23)[CH:37]=[CH:36][CH:35]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 2568102-Bromo-6-methoxypyridineHCID 86697442HCID 86697442, compound

Product 1

HCID 86697443HCID 86697443, compoundYield 67.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 65 mg (0.157 mmol) of isopropyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate in a microwave vial was added, 29 mg (0.157 mmol) of 2-bromo-6-methoxypyridine, 43 mg (0.313 mmol) of K2CO3, 18 mg (0.016 mmol) Pd(PPh3)4, 3 mL of DME and then 1 mL water. The resulting mixture was microwaved at 125° C. for 0.33 hr. It was diluted with EtOAc, washed with brine, and the organic layer dried over MgSO4. It was concentrated and purified on the neutral PREP HPLC to obtain 42 mg of the desired product. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.30 (d, J=6.32 Hz, 6 H) 3.60-3.74 (m, 4 H) 3.81 (br. s., 4 H) 4.04 (s, 3 H) 5.00 (quin, J=6.25 Hz, 1 H) 6.39 (d, J=7.83 Hz, 1 H) 6.55 (dd, J=8.08, 0.76 Hz, 1 H) 7.62 (dd, J=8.08, 7.58 Hz, 1 H) 7.83-7.93 (m, 1 H) 8.37 (d, J=7.83 Hz, 1 H) 8.66 (s, 1 H). LRMS (ESI) m/e 397 [(M+H)+, calcd for C20H24N6O3 396 ].

Workup

  1. customThe resulting mixture was microwaved at 125° C. for 0.33 hr
  2. washwashed with brine
  3. dry with materialthe organic layer dried over MgSO4
  4. concentrationIt was concentrated
  5. custompurified on the neutral PREP HPLC

Sources & evidence

ORD record
ord-672a99d4af71412a9d2a8afa3f81a768
Source dataset
uspto-grants-2015_02
Patent number
US08946415B2

Reaction notes

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