Methanol → HCID 67973596, compound

HRID 1471775Notes

Reaction equation

HRID 1471775 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20](Cl)[CH:21]=[C:16]3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:24][C:25]1[CH:30]=[C:29]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:28]=[CH:27][C:26]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].CO>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20]([C:26]4[CH:27]=[CH:28][C:29]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:30][C:25]=4[F:24])[CH:21]=[C:16]3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 447176662-Fluoro-4-(methylsulphonyl)benzeneboronic acidHCID 866748894-(5-Chlorofuro[2,3-c]pyridin-2-yl)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67973596HCID 67973596, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-(5-chloro-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (100 mg), 2-fluoro-4-(methanesulfonyl)phenylboronic acid (97 mg), 2 M aqueous Na2CO3 solution (0.33 mL), methanol (0.5 mL), and 1,4-dioxane (1.5 mL) is sparged with Ar for 10 min. PdCl2 [1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (22 mg) is added and the mixture is stirred at reflux temperature for 2 h. The mixture is diluted with water and methanol and purified by HPLC on reversed phase (methanol/water) to give the title compound. LC (method 5): tR=1.29 min; Mass spectrum (ESI+): m/z=475 [M+H]+.

Workup

  1. customis sparged with Ar for 10 min
  2. additionPdCl2 [1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (22 mg) is added
  3. temperatureat reflux temperature for 2 h
  4. additionThe mixture is diluted with water and methanol
  5. custompurified by HPLC on reversed phase (methanol/water)

Sources & evidence

ORD record
ord-09c2e1c3dc2e464790f4d2bbc60bc891
Source dataset
uspto-grants-2015_04
Patent number
US09012456B2

Reaction notes

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