Toluene → HCID 70895830, compound

HRID 72829Notes

Reaction equation

[CH3:1][N:2]([CH3:26])[C:3]1[CH:4]=[C:5]([F:25])[C:6]2[N:7]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:8]3[C:13]([S:14][C:15]=2[CH:16]=1)=[CH:12][C:11](Br)=[CH:10][CH:9]=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:86]1[CH2:91][CH2:90][O:89][CH2:88][CH2:87]1>>[CH3:1][N:2]([CH3:26])[C:3]1[CH:4]=[C:5]([F:25])[C:6]2[N:7]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:8]3[C:13]([S:14][C:15]=2[CH:16]=1)=[CH:12][C:11]([N:86]1[CH2:91][CH2:90][O:89][CH2:88][CH2:87]1)=[CH:10][CH:9]=3

Participants

Reactant 5

HCID 1140Toluene

HCID 8083Morpholine

HCID 10796Cesium carbonate

HCID 634876Binap, (A+-)-

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

Product 1

HCID 70895830HCID 70895830, compound

Procedure

To a stirred solution of 3-dimethylamino-1-fluoro-7-bromo-10-Boc-phenothiazine (14) (200 mg, 0.45 mmol) in toluene (10 mL) Pd(dba)2 (14.4 mg, 0.025 mmol), BINAP (10.9 mg, 0.018 mmol), Cs2CO3 (326 mg, 1.0 mmol) and morpholine (87 mg, 1.0 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

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-1dd41a7028c64914b2728742adfd4a1f
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828986B2

Reaction notes

Loading…