Potassium Phosphate, Tribasic → HCID 66890005, compound

HRID 1897948Notes

Reaction equation

HRID 1897948 reaction equation
Br[C:2]1[N:7]=[C:6]([CH2:8][C:9]2([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:4][CH:3]=1.[C:27]([N:31]1[C:35]([NH2:36])=[CH:34][CH:33]=[N:32]1)([CH3:30])([CH3:29])[CH3:28].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1>[C:27]([N:31]1[C:35]([NH:36][C:2]2[N:7]=[C:6]([CH2:8][C:9]3([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]3)[CH:5]=[CH:4][CH:3]=2)=[CH:34][CH:33]=[N:32]1)([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 398690981-tert-Butyl-1H-pyrazol-5-amineHCID 86649625HCID 86649625, compound

Product 1

HCID 66890005HCID 66890005, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1.33 g of 1-tert-butyl 4-ethyl 4-((6-bromopyridin-2-yl)methyl)piperidine-1,4-dicarboxylate, 650 mg of 1-tert-butyl-1H-pyrazol-5-amine (WO2007/126126, page 72, Reference 1), 360 mg of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 322 mg of tris(dibenzylideneacetone)dipalladium(0)-chloroform complex, 1.98 g of potassium phosphate and 30 ml of 1,4-dioxane was stirred at 100° C. for 4 hours, followed by cooling down to room temperature. An insoluble matter was filtered off using Celite and washed with ethyl acetate. The resulting ethyl acetate solution was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=20/1−3/2) to give the title compound as a pale brown oil.

Workup

  1. temperatureby cooling down to room temperature
  2. filtrationAn insoluble matter was filtered off
  3. washwashed with ethyl acetate
  4. concentrationThe resulting ethyl acetate solution was concentrated in vacuo
  5. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=20/1−3/2)

Sources & evidence

ORD record
ord-86ba5546b46640bf878d1da41f3c14cb
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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