Toluene → HCID 70895768, compound

HRID 72825Notes

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+].[NH:84]1[CH2:89][CH2:88][O:87][CH2:86][CH2:85]1>>[O:87]1[CH2:88][CH2:89][N:84]([C:2]2[CH:3]=[C:4]([F:24])[C:5]3[N:6]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[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)[CH2:85][CH2:86]1

Participants

Reactant 5

HCID 1140Toluene

HCID 8083Morpholine

HCID 10796Cesium carbonate

HCID 634876Binap, (A+-)-

HCID 682273243,7-Dibromo-1-fluoro-10-Boc-phenothiazine

Product 1

HCID 70895768HCID 70895768, compound

Procedure

To a stirred solution of 3,7-dibromo-1-fluoro-10-Boc-phenothiazine (8) (290 mg, 0.6 mmol) in toluene (10 mL) Pd(dba)2 (17.3 mg, 0.03 mmol), BINAP (13.5 mg, 0.02 mmol), Cs2CO3 (390 mg, 1.2 mmol) and morpholine (70 mg, 0.8 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

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

Sources & evidence

ORD record: ord-8e1ec919ab574a799495b181d763669b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828986B2

Reaction notes

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