Toluene → HCID 70895815, compound

HRID 72831Notes

Reaction equation

HRID 72831 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.C1(C)C=CC=CC=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+].[C:84]([N:91]1[CH2:97][CH2:96][CH2:95][NH:94][CH2:93][CH2:92]1)([O:86][C:87]([CH3:90])([CH3:89])[CH3:88])=[O:85]>>[C:84]([N:91]1[CH2:97][CH2:96][CH2:95][N:94]([C:2]2[CH:3]=[C:4]([F:24])[C:5]3[N:6]([C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])[C:7]4[C:12]([S:13][C:14]=3[CH:15]=2)=[CH:11][C:10]([Br:16])=[CH:9][CH:8]=4)[CH2:93][CH2:92]1)([O:86][C:87]([CH3:90])([CH3:89])[CH3:88])=[O:85]

Participants

6

Reactant 5

HCID 1140TolueneHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 682273243,7-Dibromo-1-fluoro-10-Boc-phenothiazine

Product 1

HCID 70895815HCID 70895815, compound

Procedure

To a stirred solution of 3,7-dibromo-1-fluoro-10-Boc-phenothiazine (950 mg, 2.0 mmol) in toluene (30 mL) Pd2(dba)3 (46 mg, 0.05 mmol), BINAP (31 mg, 0.05 mmol), Cs2CO3 (652 mg, 2.0 mmol) and N-Boc-homopiperazine (1-Boc-1,4-diazepane) (400 mg, 2.0 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-5c2761e4ae084696bc051f8a71c12dac
Source dataset
uspto-grants-2014_09
Patent number
US08828986B2

Reaction notes

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