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

HRID 72828Notes

Reaction equation

HRID 72828 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]>C1(C)C=CC=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]>[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

7

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 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a stirred solution of 3,7-dibromo-1-fluoro-10-Boc-phenothiazine (1.43 g, 3.0 mmol) in toluene (60 mL) in 75 mL pressure vessel Pd(dba)2 (86.3 mg, 0.15 mmol), BINAP (67.3 mg, 0.11 mmol), Cs2CO3 (978 mg, 3.0 mmol) and dimethylamine (1.5 mL, 2 M solution in THF) 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-7213fd8dcaf94606967e30e89c487aca
Source dataset
uspto-grants-2014_09
Patent number
US08828986B2

Reaction notes

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