Potassium Carbonate → 4-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-phenothiazine-10-carboxylic Acid tert-Butyl Ester

HRID 33801Notes

Reaction equation

HRID 33801 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[O:9][C:10]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:11][C:12](=[O:14])[CH:13]=1.[C:21]([O:25][C:26]([N:28]1[C:41]2[CH:40]=[CH:39][CH:38]=[C:37](B3OC(C)(C)C(C)(C)O3)[C:36]=2[S:35][C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:27])([CH3:24])([CH3:23])[CH3:22]>O1CCOCC1>[C:21]([O:25][C:26]([N:28]1[C:29]2[CH:30]=[CH:31][CH:32]=[C:33]([C:8]3[O:9][C:10]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)=[CH:11][C:12](=[O:14])[CH:13]=3)[C:34]=2[S:35][C:36]2[C:41]1=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66052622-Chloro-6-morpholinopyran-4-oneHCID 235745704-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenothiazine-10-carboxylic acid tert-butyl ester

Product 1

HCID 235745714-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-phenothiazine-10-carboxylic Acid tert-Butyl EsterYield 100.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Powdered potassium carbonate (2.03 g, 14.68 mmol) and 2-chloro-6-morpholin-4-yl-pyran-4-one (3) (1.44 g, 6.70 mmol) were added to a stirred solution of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenothiazine-10-carboxylic acid tert-butyl ester (2.85 g, 6.70 mmol) in anhydrous dioxane (20 ml) and the mixture degassed (sonication for 20 minutes then saturated with N2) thoroughly. Tetrakis (triphenylphosphine) palladium was then added in a single portion and the mixture degassed (sonication for 20 minutes then saturated with N2) once again before a reflux condenser was attached and the mixture heated to 100° C. under a nitrogen atmosphere for 20 hours. Water (30 ml) was added and the mixture extracted with EtOAc (3×30 ml). The organic extracts were then dried using MgSO4, filtered and concentrated in vacuo to yield a dark brown, crystalline solid (3.21 g, 100%) that was taken forward with no further purification. m/z (LC-MS, ESP): 479 [M+H]+, RT=4.55 mins.

Workup

  1. customthe mixture degassed (
  2. customsonication for 20 minutes
  3. additionTetrakis (triphenylphosphine) palladium was then added in a single portion
  4. customthe mixture degassed (
  5. customsonication for 20 minutes
  6. customsaturated with N2) once again before a reflux condenser was attached
  7. additionWater (30 ml) was added
  8. extractionthe mixture extracted with EtOAc (3×30 ml)
  9. customThe organic extracts were then dried
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f3d4e82e64f84a2a82aa89dafb304241
Source dataset
uspto-grants-2008_09
Patent number
US07429660B2

Reaction notes

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