Cesium carbonate → HCID 67971893, compound

HRID 1626253Notes

Reaction equation

HRID 1626253 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:24]([F:27])([F:26])[F:25])[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)=[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+].[NH:80]1[CH2:84][CH2:83][CH2:82][CH2:81]1>>[N:80]1([C:10]2[CH:11]=[C:12]3[C:7](=[CH:8][CH:9]=2)[N:6]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[C:5]2[C:4]([C:24]([F:27])([F:25])[F:26])=[CH:3][C:2]([Br:1])=[CH:15][C:14]=2[S:13]3)[CH2:84][CH2:83][CH2:82][CH2:81]1

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 31268PyrrolidineHCID 634876Binap, (A+-)-HCID 67467063HCID 67467063, compound

Product 1

HCID 67971893HCID 67971893, compound

Procedure

To a stirred solution of 3,7-dibromo-1-trifluoromethyl-10-Boc-phenothiazine (18) (104 mg, 0.2 mmol) in xylenes (5 mL) Pd(dba)2 (5.8 mg, 0.01 mmol), BINAP (4.4 mg, 0.007 mmol), Cs2CO3 (325 mg, 1.0 mmol) and pyrrolidine (0.017 mL, 14.2 mg, 0.2 mmol) were added. The mixture was refluxed for 48 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 48 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-e9075f3f129a4b48af1f93271e31d7e8
Source dataset
uspto-grants-2014_07
Patent number
US08785434B2

Reaction notes

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