Tris(1,1-dimethylethyl)phosphine → HCID 59713805, compound

HRID 2223073Notes

Reaction equation

HRID 2223073 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6](B(O)O)=[CH:5][N:4]=1.[F-].[K+].Cl[C:17]1[C:23]2[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=2[N:21]([CH3:29])[C:20](=[O:30])[CH2:19][N:18]=1.P(C(C)(C)C)(C(C)(C)C)C(C)(C)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:28][C:25]1[CH:26]=[CH:27][C:22]2[N:21]([CH3:29])[C:20](=[O:30])[CH2:19][N:18]=[C:17]([C:6]3[C:7]([O:9][CH3:10])=[N:8][C:3]([O:2][CH3:1])=[N:4][CH:5]=3)[C:23]=2[CH:24]=1

Participants

6

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 522689Potassium FluorideHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 123385855,7-Dichloro-1-methyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

Product 1

HCID 59713805HCID 59713805, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

As illustrated in the scheme above and following General Procedure 5, (2,4-dimethoxy-5-pyrimidinyl)boronic acid (0.939 g, 5.10 mmol), Pd2(dba)3 (0.064 g, 0.07 mmol), dry KF (0.890 g, 15.3 mmol), 5,7-dichloro-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (1.12 g, 4.61 mmol) and P(t-Bu)3 (0.42 mL of a 10% solution in hexanes, 0.21 mmol) were combined and heated for 20 h. After workup, purification of the crude product by silica gel column chromatography (1:3 hexanes:EtOAc) provided the title compound as a pale orange solid (1.20 g, 75%). 1H-NMR (CDCl3): δ 8.50 (s, 1H), 7.49 (dd, J=2.4 Hz, J=8.8 Hz, 1H), 7.29 (d, J=8.8 Hz, 1H), 7.13 (d, J=2.4 Hz, 1H), 4.84 (d, J=10.8 Hz, 1H), 4.06 (s, 3H), 3.79 (s, 3H), 3.76 (d, J=10.8 Hz, 1H), 3.42 (s, 3H). MS (ESI) (M+H)+=347.

Workup

  1. temperatureheated for 20 h
  2. customAfter workup, purification of the crude product by silica gel column chromatography (1:3 hexanes:EtOAc)

Sources & evidence

ORD record
ord-a80e8eee729f4999b4ce1d80e025defc
Source dataset
uspto-grants-2008_05
Patent number
US07375101B2

Reaction notes

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