Triethylamine → HCID 86607282, compound

HRID 1726404Notes

Reaction equation

HRID 1726404 reaction equation
Br[C:2]1[C:3]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[N:4][N:5]2[CH:10]=[CH:9][CH:8]=[N:7][C:6]=12.[CH3:17][O:18]/[N:19]=[C:20]1\[CH2:21][CH2:22][C:23]2[C:28]\1=[CH:27][CH:26]=[C:25](B(O)O)[CH:24]=2.C(N(CC)CC)C>COCCOC.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(OCC)(=O)C>[CH3:17][O:18][N:19]=[C:20]1[C:28]2[C:23](=[CH:24][C:25]([C:2]3[C:3]([C:11]4[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=4)=[N:4][N:5]4[CH:10]=[CH:9][CH:8]=[N:7][C:6]=34)=[CH:26][CH:27]=2)[CH2:22][CH2:21]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 17976063HCID 17976063, compoundHCID 68928937HCID 68928937, compound

Product 1

HCID 86607282HCID 86607282, compoundYield 49%

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
60 °C

Procedure

To 3-bromo-2-(pyridin-4-yl)pyrazolo[1.5-a]pyrimidine (0.150 g; Example 7, step 4) and (E)-1-(methoxyimino)-2,3-dihydro-1H-inden-5-ylboronic acid (0.224 g; Example 1, Step 5) in 5.5 mL 1,2-dimethoxyethane, was added 0.167 mL triethylamine and 27 mg 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride catalyst. The mixture was heated at 60° C. for 16 hours, diluted with ethyl acetate, and washed with 10% aqueous potassium carbonate, dried over sodium sulfate, filtered, and evaporated to yield 94 mg (49% yield) product as a yellow solid. 1H NMR (CDCl3) was consistent with the desired structure. MS showed a M+1 molecular ion of m/z 356.2 by positive APCI.

Workup

  1. washwashed with 10% aqueous potassium carbonate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-c1694c573bed473ca711b0817340968e
Source dataset
uspto-grants-2009_02
Patent number
US07491829B2

Reaction notes

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