Cesium carbonate → HCID 67463501, compound

HRID 1626254Notes

Reaction equation

[N:1]1([C:6]2[CH:7]=[C:8]3[C:17](=[CH:18][CH:19]=2)[N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:15]2[C:14]([C:27]([F:30])([F:29])[F:28])=[CH:13][C:12](Br)=[CH:11][C:10]=2[S:9]3)[CH2:5][CH2:4][CH2:3][CH2:2]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+].[CH3:84][N:85]1[CH2:90][CH2:89][NH:88][CH2:87][CH2:86]1>>[CH3:84][N:85]1[CH2:90][CH2:89][N:88]([C:12]2[CH:13]=[C:14]([C:27]([F:30])([F:29])[F:28])[C:15]3[N:16]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[C:17]4[C:8]([S:9][C:10]=3[CH:11]=2)=[CH:7][C:6]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:19][CH:18]=4)[CH2:87][CH2:86]1

Participants

Reactant 4

HCID 10796Cesium carbonate

HCID 531671-Methylpiperazine

HCID 634876Binap, (A+-)-

HCID 67971893HCID 67971893, compound

Product 1

HCID 67463501HCID 67463501, compound

Procedure

To a stirred solution of 7-(pyrrolidin-1-yl)-3-bromo-1-trifluoromethyl-10-Boc-phenothiazine (30 mg, 0.058 mmol) in xylenes (5 mL) Pd(dba)2 (1.7 mg, 0.003 mmol), BINAP (1.3 mg, 0.002 mmol), Cs2CO3 (94.5 mg, 0.29 mmol) and 1-methylpiperazine (8.7 mg, 0.01 mL, 0.087 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

temperatureThe mixture was refluxed for 48 h
filtrationAfter that reaction mixture was filtered
customsolvent was removed under vacuum
customProduct was used without additional purification

Sources & evidence

ORD record: ord-851de2b8beb74a6dbbe4f7546d4a49f8
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785434B2

Reaction notes

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