Toluene → HCID 70895826, compound

HRID 72832Notes

Reaction equation

HRID 72832 reaction equation
[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:16]=[C:17]([F:37])[C:18]3[N:19]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:20]4[C:25]([S:26][C:27]=3[CH:28]=2)=[CH:24][C:23](Br)=[CH:22][CH:21]=4)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].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:97]1[CH2:102][CH2:101][O:100][CH2:99][CH2:98]1>>[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:16]=[C:17]([F:37])[C:18]3[N:19]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:20]4[C:25]([S:26][C:27]=3[CH:28]=2)=[CH:24][C:23]([N:97]2[CH2:102][CH2:101][O:100][CH2:99][CH2:98]2)=[CH:22][CH:21]=4)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 5

HCID 1140TolueneHCID 8083MorpholineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 70895815HCID 70895815, compound

Product 1

HCID 70895826HCID 70895826, compound

Procedure

To a stirred solution of 3-(4-Boc-1,4-diazepan-1-yl)-1-fluoro-7-bromo-10-Boc-phenothiazine (1.1 g, 2.0 mmol) in toluene (10 mL) Pd2(dba)3 (46 mg, 0.05 mmol), BINAP (31 mg, 0.018 mmol), Cs2CO3 (652 mg, 2.0 mmol) and morpholine (348 mg, 4.0 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-24a2ff0ae4da4ba684f4087e36bdd10b
Source dataset
uspto-grants-2014_09
Patent number
US08828986B2

Reaction notes

Loading…