Triethylborane → HCID 24823898, compound

HRID 2355092Notes

Reaction equation

HRID 2355092 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:21]=[CH:20][C:14]3[O:15][C:16]([F:19])([F:18])[O:17][C:13]=3[CH:12]=2)=[O:10])=[CH:4][C:3]=1[C:22](=[O:44])[NH:23][C:24]1[CH:25]=[N:26][C:27]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([N:37]3[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]3)=[CH:33][CH:32]=2)=[N:28][CH:29]=1.[CH:45]1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCC[CH2:46]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(B(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[CH2:45]([C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:21]=[CH:20][C:14]3[O:15][C:16]([F:19])([F:18])[O:17][C:13]=3[CH:12]=2)=[O:10])=[CH:4][C:3]=1[C:22](=[O:44])[NH:23][C:24]1[CH:25]=[N:26][C:27]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([N:37]3[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]3)=[CH:33][CH:32]=2)=[N:28][CH:29]=1)[CH3:46]

Participants

7

Reactant 4

HCID 7357TriethylboraneHCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 24823740HCID 24823740, compound

Product 1

HCID 24823898HCID 24823898, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A resealable tube was charged with N-(4-chloro-3-((2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrimidin-5-yl)carbamoyl)phenyl)-2,2-difluorobenzo[d][1,3]dioxole-5-carboxamide 38 (0.050 g, 0.080 mmol), palladium(II) acetate (0.0018 g, 0.0080 mmol), 2-(dicyclohexylphosphino)-2′,6′-dimethoxy-1,1′-biphenyl (0.0066 g, 0.016 mmol), potassium phosphate (0.068 g, 0.32 mmol), and DMF (2.0 mL). A solution of triethylborane (0.12 mL, 0.12 mmol) (1M in THF) was added. The reaction tube was evacuated and purged with argon, and then sealed. The mixture stirred at 100° C. for 6 h. The reaction mixture was filtered through a pad of Celite and concentrated to afford a yellow green solid. This material was purified via preparative thin layer chromatography (eluting three times with 95:5:0.5, dichloromethane/methanol/ammonium hydroxide) to afford N-(4-ethyl-3-((2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrimidin-5-yl)carbamoyl)phenyl)-2,2-difluorobenzo[d][1,3]dioxole-5-carboxamide 39 as an off-white solid. MS m/z found 616.2 [MH+]; calc. for C32H31F2N7O4=615.63.

Workup

  1. customThe reaction tube was evacuated
  2. custompurged with argon
  3. customsealed
  4. filtrationThe reaction mixture was filtered through a pad of Celite
  5. concentrationconcentrated
  6. customto afford a yellow green solid
  7. customThis material was purified via preparative thin layer chromatography (eluting three times with 95:5:0.5, dichloromethane/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-336980d8ec3b4449a759ca0878c40318
Source dataset
uspto-grants-2010_07
Patent number
US07754717B2

Reaction notes

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