Pyridine → HCID 70656373, compound

HRID 872850Notes

Reaction equation

HRID 872850 reaction equation
B1([C:7]2[CH:12]=[CH:11][CH:10]=[N:9][CH:8]=2)OCCCO1.[Cl:13][C:14]1[CH:15]=[C:16]([C:23]2[CH:27]=[CH:26][N:25]([CH2:28][C@@H:29]([NH:31][C:32]([C:34]3[N:35]=[CH:36][NH:37][CH:38]=3)=[O:33])[CH3:30])[N:24]=2)[CH:17]=[C:18]([F:22])[C:19]=1[C:20]#[N:21].N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(Cl)Cl>[Cl:13][C:14]1[CH:15]=[C:16]([C:23]2[CH:27]=[CH:26][N:25]([CH2:28][C@@H:29]([NH:31][C:32]([C:34]3[N:35]=[CH:36][N:37]([C:7]4[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=4)[CH:38]=3)=[O:33])[CH3:30])[N:24]=2)[CH:17]=[C:18]([F:22])[C:19]=1[C:20]#[N:21]

Participants

6

Reactant 3

HCID 1049PyridineHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 178461760HCID 178461760, compound

Product 1

HCID 70656373HCID 70656373, compoundYield 16.57%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

3-Pyridineboronic acid 1,3-propanediol ester (43.7 mg, 0.268 mmol), (S)—N-(1-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-imidazole-4-carboxamide (50 mg, 0.134 mmol), anhydrous copper(II) acetate (36.5 mg, 0.201 mmol), pyridine (0.022 ml, 0.268 mmol) and DCM (1 ml) were added into a flask and stirred at RT for 47 h. The reaction mixture was extracted with ethyl acetate, dried, filtered and evaporated. The product was purified by column chromatography. Yield 16.57%. 1H-NMR (400 MHz; CDCl3): δ 1.24 (d, 3H), 4.28 (dd, 1H), 4.47 (dd, 1H), 4.57-4.67 (m, 1H), 6.64 (d, 1H), 7.48-7.55 (m, 2H), 7.74-7.78 (m, 1H), 7.81 (d, 1H), 7.88 (d, 1H), 7.91-7.94 (m, 2H), 8.27 (d, 1H), 8.72 (d, 1H), 8.79 (d, 1H).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. customdried
  3. filtrationfiltered
  4. customevaporated
  5. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-74d446da2ddb4e50ac9350a63755bdc1
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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