2-Fluoro-4-(methylsulphonyl)aniline → tert-butyl 4-(4-{[2-fluoro-4-(methylsulfonyl)phenyl]amino}-5H-pyrrolo[3,2-d]pyrimidin-7-yl)piperidine-1-carboxylic acid

HRID 1616089Notes

Reaction equation

HRID 1616089 reaction equation
Cl[C:2]1[C:3]2[NH:10][CH:9]=[C:8]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19]C(C)(C)C)=[O:18])[CH2:13][CH2:12]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[F:24][C:25]1[CH:31]=[C:30]([S:32]([CH3:35])(=[O:34])=[O:33])[CH:29]=[CH:28][C:26]=1[NH2:27].[C:36](O[Na])([CH3:39])([CH3:38])[CH3:37]>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:36]([CH:13]1[CH2:12][CH:11]([C:8]2[C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH:27][C:26]4[CH:28]=[CH:29][C:30]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:31][C:25]=4[F:24])[C:3]=3[NH:10][CH:9]=2)[CH2:16][CH2:15][N:14]1[C:17]([OH:19])=[O:18])([CH3:39])([CH3:38])[CH3:37]

Participants

6

Reactant 3

HCID 27833852-Fluoro-4-(methylsulphonyl)anilineHCID 86681880tert-butyl 4-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-7-yl)piperidine-1-carboxylateHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 86681881tert-butyl 4-(4-{[2-fluoro-4-(methylsulfonyl)phenyl]amino}-5H-pyrrolo[3,2-d]pyrimidin-7-yl)piperidine-1-carboxylic acidYield 6.7%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 4-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-7-yl)piperidine-1-carboxylate (54.8 mg, 0.163 mmol) was dissolved in 1,4-dioxane (0.5 mL), 2-fluoro-4-methylsulfonylaniline (32.0 mg, 0.169 mmol), tert-butoxysodium (15.9 mg, 0.109 mmol) and bis(tri-tert-butyl-phosphine)palladium (0) (5.8 mg, 0.011 mmol) were added, and the mixture was irradiated with microwave in a sealed tube at 130° C. for 3 hours. The reaction liquid was filtered, the filtrate was concentrated under a reduced pressure, and the obtained residue was purified by using silica gel chromatography (ethyl acetate:hexane=3:1) to give the titled compound (3.6 mg, 6.5%) as a white amorphous.

Workup

  1. customthe mixture was irradiated with microwave in a sealed tube at 130° C. for 3 hours
  2. customThe reaction liquid
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated under a reduced pressure
  5. customthe obtained residue was purified

Sources & evidence

ORD record
ord-d182c8989b3c46a39ea7d9980488f043
Source dataset
uspto-grants-2014_07
Patent number
US08765771B2

Reaction notes

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