Cesium carbonate → HCID 70895770, compound

HRID 72826Notes

Reaction equation

HRID 72826 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([F:29])[C:10]3[N:11]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:12]4[C:17]([S:18][C:19]=3[CH:20]=2)=[CH:16][C:15](Br)=[CH:14][CH:13]=4)[CH2:3][CH2:2]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].[NH:82]1[CH2:86][CH2:85][CH2:84][CH2:83]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]>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([F:29])[C:10]3[N:11]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:12]4[C:17]([S:18][C:19]=3[CH:20]=2)=[CH:16][C:15]([N:82]2[CH2:86][CH2:85][CH2:84][CH2:83]2)=[CH:14][CH:13]=4)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 31268PyrrolidineHCID 634876Binap, (A+-)-HCID 70895768HCID 70895768, compound

Product 1

HCID 70895770HCID 70895770, compound

Reagents, catalysts & solvents 1

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalyst

Procedure

To a stirred solution of 3-morpholino-1-fluoro-7-bromo-10-Boc-phenothiazine (150 mg, 0.3 mmol) in touene (10 mL) Pd(dba)2 (5.8 mg, 0.01 mmol), BINAP (6.3 mg, 0.01 mmol), Cs2CO3 (326 mg, 1.0 mmol) and pyrrolidine (42.6 mg, 0.6 mmol) were added. The mixture was refluxed for 24 h. After that reaction mixture was filtered, solvent was removed under vacuum. Product was used without additional purification.

Workup

  1. temperatureThe mixture was refluxed for 24 h
  2. filtrationAfter that reaction mixture was filtered
  3. customsolvent was removed under vacuum
  4. customProduct was used without additional purification

Sources & evidence

ORD record
ord-e747b531ab19433e97189060ba8c624b
Source dataset
uspto-grants-2014_09
Patent number
US08828986B2

Reaction notes

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