N-(2-(p-bromophenoxy)ethyl)pyrrolidine → HCID 59589762, compound

HRID 1472834Notes

Reaction equation

HRID 1472834 reaction equation
[CH3:1][S:2][C:3]1[N:8]2[N:9]=[C:10]([NH2:12])[N:11]=[C:7]2[CH:6]=[CH:5][CH:4]=1.Br[C:14]1[CH:27]=[CH:26][C:17]([O:18][CH2:19][CH2:20][N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:16][CH:15]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[Na+]>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].CN(C)C(=O)C.O1CCOCC1>[CH3:1][S:2][C:3]1[N:8]2[N:9]=[C:10]([NH:12][C:14]3[CH:15]=[CH:16][C:17]([O:18][CH2:19][CH2:20][N:21]4[CH2:22][CH2:23][CH2:24][CH2:25]4)=[CH:26][CH:27]=3)[N:11]=[C:7]2[CH:6]=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 70657N-(2-(p-bromophenoxy)ethyl)pyrrolidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 59589724HCID 59589724, compound

Product 1

HCID 59589762HCID 59589762, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

A microwave vial containing 5-methylsulfanyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (13.5 g, 74.9 mmol), 1-(2-(4-bromophenoxy)ethyl)pyrrolidine (20.2 mL, 97.3 mmol), tris(dibenzylideneacetone)dipalladium (3.42 g, 3.74 mmol), xantphos (4.33 g, 7.49 mmol), sodium tert-butoxide (14.7 g, 150 mmol) and 1,4-dioxane (90 mL) was heated under microwave radiation (150° C., 10 min). N,N-Dimethylacetamide (1 mL) was added to assist with microwave absorption. The volatiles were removed under rotary evaporation and the product then purified by graduated flash column chromatography (2-10% methanol: dichloromethane) to provide a pale brown solid. Yield: 19.3 g, 70%; LCMS method: 2, RT: 2.28 min, MI: 370 [M+1]. 1H NMR (CDCl3, 300 MHz): 7.53 (d, 2H), 7.40 (d 1H), 7.26 (d, 1H), 7.10 (s, 1H), 6.93 (d 2H), 6.64 (d, 1H), 4.11 (t, 2H), 2.90 (t, 2H), 2.64 (s, 7H), 1.81 (s, 4H).

Workup

  1. customto assist with microwave absorption
  2. customThe volatiles were removed under rotary evaporation
  3. customthe product then purified by graduated flash column chromatography (2-10% methanol: dichloromethane)
  4. customto provide a pale brown solid

Sources & evidence

ORD record
ord-4d6c900cef8148dd9ac7eb36974b3035
Source dataset
uspto-grants-2015_04
Patent number
US09012633B2

Reaction notes

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