1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 66710172, compound

HRID 1256044Notes

Reaction equation

HRID 1256044 reaction equation
Br[C:2]1[C:3]([C:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[NH:32][CH:31]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][CH:18]([N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)[CH2:17][CH2:16]3)=[CH:11][C:10]=2[O:28][CH3:29])=[N:6][CH:7]=1.[C:39]([Zn]C#N)#[N:40].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>CC(N(C)C)=O.[Zn].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]>[NH:32]1[C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:30]([C:3]2[C:2]([C:39]#[N:40])=[CH:7][N:6]=[C:5]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([N:15]4[CH2:16][CH2:17][CH:18]([N:21]5[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]5)[CH2:19][CH2:20]4)=[CH:11][C:10]=3[O:28][CH3:29])[N:4]=2)=[CH:31]1

Participants

7

Reactant 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 58071454HCID 58071454, compoundHCID 178514179HCID 178514179, compound

Product 1

HCID 66710172HCID 66710172, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 31374DimethylacetamideSolvent

Procedure

5-Bromo-4-(1H-indol-3-yl)-N-(2-methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)phenyl)pyrimidin-2-amine (Example 27, 155 mg, 0.27 mmol), zinc powder (0.176 mg, 2.69 μmol), dicyanozinc (47.4 mg, 0.40 mmol), Pd2dba3 (12.31 mg, 0.01 mmol), and xantphos (15.56 mg, 0.03 mmol) in DMA (1.5 mL) were heated at 130° C. for 2 h. The reaction mixture was purified by chromatography on silica gel (10% MeOH/1% NH4OH in DCM) to give the title product (73.0 mg, 52.0%).

Workup

  1. customThe reaction mixture was purified by chromatography on silica gel (10% MeOH/1% NH4OH in DCM)

Sources & evidence

ORD record
ord-22adb7e6f1364428ad2449bc9a94f343
Source dataset
uspto-grants-2013_06
Patent number
US08461170B2

Reaction notes

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