Diisopropylethylamine → HCID 66955956, compound

HRID 1399719Notes

Reaction equation

HRID 1399719 reaction equation
Cl[C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:16])[N:5]=[C:4]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[N:3]=1.C(N(CC)C(C)C)(C)C.[CH2:32]1[C:42]2=[C:43]3[C:38](=[CH:39][CH:40]=[CH:41]2)[C:37](B2OC(C)(C)C(C)(C)O2)=[CH:36][CH:35]=[C:34]3[CH2:33]1>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:33]1[C:34]2=[C:43]3[C:38](=[CH:37][CH:36]=[CH:35]2)[C:39]([C:2]2[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:16])[N:5]=[C:4]([N:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)[N:3]=2)=[CH:40][CH:41]=[C:42]3[CH2:32]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 222401402-(1,2-Dihydroacenaphthylen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86665653Methyl 2-(4-chloro-6-methyl-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoate

Product 1

HCID 66955956HCID 66955956, compoundYield 36.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

This compound was prepared according to general method E from methyl 2-(4-chloro-6-methyl-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoate (0.081 g; 0.25 mmol), tetrakis(triphenylphosphine) palladium(0) (0.029 g; 0.025 mmol), N,N-diisopropylethylamine (0.172 mL; 1.00 mmol) and 2-(1,2-dihydroacenaphthylen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.105 g; 0.375 mmol) in DME-water (1 mL) for 20 min. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (1-10%) in heptane furnished 0.040 g (36%) of the title compound as a yellow oil.

Workup

  1. customThis compound was prepared
  2. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (1-10%) in heptane

Sources & evidence

ORD record
ord-718ff851e0134d5a9f1e022a389f4d93
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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