3-Nitrophenylboronic Acid → HCID 68274526, compound

HRID 628996Notes

Reaction equation

HRID 628996 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[C:5]([O:14][CH3:15])=[CH:4][N:3]=1.[N+:16]([C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1)([O-:18])=[O:17].C([O-])([O-])=O.[Na+].[Na+]>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>[CH3:15][O:14][C:5]1[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:7][C:2]([C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:16]([O-:18])=[O:17])[CH:24]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 86668896HCID 86668896, compound

Product 1

HCID 68274526HCID 68274526, compoundYield 39.97%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(2-chloro-5-methoxy-pyrimidin-4-yl)-morpholine (0.2 g, 1.0 eq), 3-nitrophenyl boronic acid (0.17 g, 1.2 eq), (PPh3)4Pd (0.10 g, 0.1 eq) and 2 M Na2CO3 (1.3 ml, 3.0 eq) was heated at 80° C. and refluxed overnight. The solvent was removed in vacuo, and the residue was extracted with EA and water. The combined organic layers were washed with brine, dried and evaporated in vacuo. The crude was purified by chromatography to give a yellow solid (0.11 g, 39.97%).

Workup

  1. temperaturerefluxed overnight
  2. customThe solvent was removed in vacuo
  3. extractionthe residue was extracted with EA and water
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. customevaporated in vacuo
  7. customThe crude was purified by chromatography

Sources & evidence

ORD record
ord-37e23a5748214b43a68a970e104b6b72
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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