Dimethylamine → 3-Dimethylamino-1-fluoro-7-bromo-10-Boc-phenothiazine

HRID 408119Notes

Reaction equation

HRID 408119 reaction equation
Br[C:2]1[CH:3]=[C:4]([F:24])[C:5]2[N:6]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:7]3[C:12]([S:13][C:14]=2[CH:15]=1)=[CH:11][C:10]([Br:16])=[CH:9][CH:8]=3.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+].[CH3:77][NH:78][CH3:79]>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]>[CH3:77][N:78]([CH3:79])[C:2]1[CH:3]=[C:4]([F:24])[C:5]2[N:6]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:7]3[C:12]([S:13][C:14]=2[CH:15]=1)=[CH:11][C:10]([Br:16])=[CH:9][CH:8]=3

Participants

6

Reactant 4

HCID 674DimethylamineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 682273243,7-Dibromo-1-fluoro-10-Boc-phenothiazine

Product 1

HCID 682273403-Dimethylamino-1-fluoro-7-bromo-10-Boc-phenothiazine

Reagents, catalysts & solvents 1

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

Procedure

To a stirred solution of 3,7-dibromo-1-fluoro-10-Boc-phenothiazine (8) (475 mg, 1 mmol) in touene (10 mL) Pd(dba)2 (28.9 mg, 0.05 mmol), BINAP (22.5 mg, 0.035 mmol), Cs2CO3 (652 mg, 2 mmol) and dimethylamine (0.6 mL, 1.2 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-4ec46acf52b04c1aacb04176e326f276
Source dataset
uspto-grants-2014_06
Patent number
US08759336B2

Reaction notes

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