Sodium Carbonate → tert-butyl 4-{2-[4-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-(trifluoromethyl)phenoxy]ethyl}piperidine-1-carboxylate

HRID 522272Notes

Reaction equation

HRID 522272 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:30]=[CH:29][C:12]([O:13][CH2:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)=[C:11]([C:31]([F:34])([F:33])[F:32])[CH:10]=2)O1.C([O-])([O-])=O.[Na+].[Na+].[Cl:42][C:43]1[N:44]=[C:45](Cl)[C:46]2[CH:51]=[CH:50][NH:49][C:47]=2[N:48]=1.O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O.O>[Cl:42][C:43]1[N:44]=[C:45]([C:9]2[CH:30]=[CH:29][C:12]([O:13][CH2:14][CH2:15][CH:16]3[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[CH2:20][CH2:21]3)=[C:11]([C:31]([F:32])([F:34])[F:33])[CH:10]=2)[C:46]2[CH:51]=[CH:50][NH:49][C:47]=2[N:48]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 141168712,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidineHCID 67294312Tert-butyl 4-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)phenoxy)ethyl)piperidine-1-carboxylate

Product 1

HCID 90065716tert-butyl 4-{2-[4-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-(trifluoromethyl)phenoxy]ethyl}piperidine-1-carboxylateYield 43.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

After tert-butyl 4-{2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)phenoxy]ethyl}piperidine-1-carboxylate (266 mg), Na2CO3 (169 mg), and tetrakis(triphenylphosphine)palladium (0) (31 mg) were added to a mixture of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (100 mg), dioxane (1.6 mL), and water (0.6 mL), the mixture was stirred at 150° C. for 2 hours under microwave irradiation, and cooled to room temperature. After water and EtOAc were added to the reaction mixture, the mixture was stirred, filtered, and washed with EtOAc, whereby tert-butyl 4-{2-[4-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-(trifluoromethyl)phenoxy]ethyl}piperidine-1-carboxylate (121 mg) was obtained as a brown solid.

Workup

  1. temperaturecooled to room temperature
  2. stirringthe mixture was stirred
  3. filtrationfiltered
  4. washwashed with EtOAc

Sources & evidence

ORD record
ord-a259ba364a314e9d89042d12909ac577
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Reaction notes

Loading…