1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 25108481, compound

HRID 383872Notes

Reaction equation

HRID 383872 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:23])[C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:24][C:25]1[C:26]([F:38])=[C:27]([C:31]2[CH:36]=[CH:35][N:34]=[C:33]([NH2:37])[N:32]=2)[CH:28]=[CH:29][CH:30]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:24][C:25]1[C:26]([F:38])=[C:27]([C:31]2[CH:36]=[CH:35][N:34]=[C:33]([NH:37][C:2]3[CH:3]=[C:4]([NH:8][C:9](=[O:23])[C:10]4[CH:15]=[CH:14][C:13]([CH2:16][N:17]5[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]5)=[CH:12][CH:11]=4)[CH:5]=[CH:6][CH:7]=3)[N:32]=2)[CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 2806200HCID 2806200, compoundHCID 19062908HCID 19062908, compound

Product 1

HCID 25108481HCID 25108481, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of N-(3-bromophenyl)-4-(piperidin-1-ylmethyl)benzamide (20 mg, 0.054 mmol) and 4-(3-chloro-2-fluorophenyl)pyrimidin-2-amine (18 mg, 0.080 mmol), KOBut (12 mg, 0.11 mmol), Pd2(dba)3 (2.5 mg, 0.027 mmol) and Xantphos (2.5 mg, 0.043 mmol) in a microwave reaction vessel was suspended in 0.6 mL of toluene. The reaction mixture was heated in a microwave at 150° C. for 1 h. After cooling, the mixture was diluted with DMF, and then filtered with a 0.45 μm microfilter. The obtained filtrate was separated by a semi-preparative HPLC. Collected product fraction was lyophilized to give pure product as a while powder. MS (ESI+) m/z 516.2 [M+H]+.

Workup

  1. customin a microwave reaction vessel
  2. temperatureAfter cooling
  3. filtrationfiltered with a 0.45 μm microfilter
  4. customThe obtained filtrate was separated by a semi-preparative HPLC
  5. customto give pure product as a while powder

Sources & evidence

ORD record
ord-403fc1877f9449a89c3e8ad4ff009a25
Source dataset
uspto-grants-2013_02
Patent number
US08367686B2

Reaction notes

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