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Cesium carbonate → HCID 10226975, compound

HRID 2416636
Notes
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Reaction equation

HRID 2416636 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]3[CH:13]=[CH:14][C:15]([C:17]4[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24](=[O:26])[CH3:25])[N:18]=4)=[CH:16][C:9]=23)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:33][O:34][C:35]1[N:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37](B(O)O)[N:36]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC=CC=1>[CH3:33][O:34][C:35]1[N:40]=[C:39]([C:2]2[CH:3]=[C:4]([C:8]3[O:12][N:11]=[C:10]4[CH:13]=[CH:14][C:15]([C:17]5[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24](=[O:26])[CH3:25])[N:18]=5)=[CH:16][C:9]=34)[CH:5]=[CH:6][CH:7]=2)[C:38]([O:41][CH3:42])=[CH:37][N:36]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 22632293HCID 22632293, compoundHCID 22632309(2,5-Dimethoxypyrimidin-4-yl)boronic acid

Product 1

HCID 10226975HCID 10226975, compoundYield 13%

Reagents, catalysts & solvents 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 241BenzeneSolvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A flask was charged with N-{4-[3-(3-bromophenyl)-benzo[c]isoxazol-5-yl]-pyrimidin-2-yl}-acetamide (100 mg, 0.272 mmol), cesium carbonate (97.7 mg, 0.328 mmol), and 2,5-dimethoxypyrimidine-6-boronic acid (55.0 mg, 0.3 mmol). The flask was evacuated and back-filled with nitrogen 5-7 times before adding 5 mL of degassed p-dioxane and 1 mL of degassed DMF. To this stirring solution/suspension was added, 125 μL of a 10% w/v benzene solution of tri-tertbutylphosphine followed by the addition of Pd2(dba)3 (25 mg, 0.0272 mmol) slurred in 1 mL of degassed DMF. The reaction was stirred under nitrogen atmosphere, at 80° C. Reaction was followed by HPLC and deemed to be complete in 4 hours. The reaction mixture was suction filtered hot through a pad of diatomaceous earth and washed the precipitate with DMF and acetonitrile. The filtrate was reduced to an oil under reduced pressure and the crude material purified via HPLC utilizing acetonitrile/water/TFA as the eluent. The material was isolated as a bright yellow powder (15 mg, 13% yield). 1H NMR (500 MHz DMSO-d6) δ 8.93 (s, 1H) 8.6 (s, 1H), 8.31 (s, 1H), 8.29 (d, 1H), 8.25 (d, 1H), 8.07 (d, 1H), 7.87 (d, 1H), 7.81 (d, 1H), 7.77 (m, 1H), 4.02 (2 close sing, 6H) in ppm. LC-MS (ES+) m/e=469 (M+H)

Workup

  1. customThe flask was evacuated
  2. additionback-filled with nitrogen 5-7 times
  3. additionbefore adding 5 mL of degassed p-dioxane and 1 mL of degassed DMF
  4. additionTo this stirring solution/suspension was added
  5. customReaction
  6. filtrationfiltered hot through a pad of diatomaceous earth
  7. washwashed the precipitate with DMF and acetonitrile
  8. customthe crude material purified via HPLC

Sources & evidence

ORD record
ord-e218a46ff184455aa014c4ab6c0e6a4f
Source dataset
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06825190B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes