N-(2-(p-bromophenoxy)ethyl)pyrrolidine → HCID 59589976, compound

HRID 1971607

Reaction equation

HRID 1971607 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:16]4[N:17]=[C:18]([NH2:20])[N:19]=[C:15]4[CH:14]=[CH:13][C:12]=3[O:21][CH3:22])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.Br[C:24]1[CH:37]=[CH:36][C:27]([O:28][CH2:29][CH2:30][N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:26][CH:25]=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+]>CC(N(C)C)=O.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].O1CCOCC1>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:16]4[N:17]=[C:18]([NH:20][C:24]5[CH:25]=[CH:26][C:27]([O:28][CH2:29][CH2:30][N:31]6[CH2:32][CH2:33][CH2:34][CH2:35]6)=[CH:36][CH:37]=5)[N:19]=[C:15]4[CH:14]=[CH:13][C:12]=3[O:21][CH3:22])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]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 595896845-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-6-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Product 1

HCID 59589976HCID 59589976, compound

Reagents, catalysts & solvents 3

HCID 31374DimethylacetamideCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

In a microwave vial, 5-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-6-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (0.05 g, 0.17 mmol), 1-[2-(4-bromophenoxy)ethyl]-pyrrolidine (0.068 g, 0.251 mmol), bis(dibenzylideneacetone)palladium (0.005 g, 0.008 mmol), Xantphos (0.01 g, 0.017 mmol) and sodium tert-butoxide (0.033 g, 0.335 mmol) were added successively. Dioxane (1.2 mL) and dimethylacetamide (2 drops) were added and the vial was sealed and heated in the microwave (150° C., 10 min). The crude was purified using an SCX cartridge, by washing with methanol and releasing the compound with 2M ammonia in methanol. After concentration under reduced pressure, the crude was purified by preparatory LCMS. LCMS Method: 2: RT: 2.52 min, MI: 488 [M+1].

Workup

  1. customthe vial was sealed
  2. customThe crude was purified
  3. washby washing with methanol
  4. concentrationAfter concentration under reduced pressure
  5. customthe crude was purified by preparatory LCMS

Sources & evidence

ORD record
ord-03eab5ab938e4f9aaeb9115a72607a58
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Linked notes

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